2-Ethoxyethyl acetate, Safety
2-Ethoxyethyl acetate can cause a slight skin and eye irritation after exposure. High exposure can lead to kidney damage and paralysis. In animals, reproductive and teratogenic effects have been observed.


2-Ethyl-1-butanol
2-Ethyl-1-butanol (IUPAC name: 2-ethylbutan-1-ol) is an organic chemical compound. It can be used to facilitate the separation of ethanol from water, which form an azeotrope that otherwise limits the maximum ethanol concentration.


2-Ethyl-1-butanol, Reactions
2-Ethyl-1-butanol is manufactured industrially by the aldol condensation of acetaldehyde and butyraldehyde, followed by hydrogenation. It may also be prepared by the Guerbet reaction.


2-Ethyl-1-butanol, Properties and applications
The branching in 2-ethyl-1-butanol makes it harder to crystalize due to packing disruption, which results in a very low freezing point. Esters of 2-ethyl-1-butanol are similarly effected and it therefore finds application as a feedstock in the production of plasticizers and lubricants, where its presence helps reduce viscosity and lower freezing points.


2-Ethyl-2-oxazoline
2-Ethyl-2-oxazoline (EtOx) is an oxazoline which is used particularly as a monomer for the cationic ring-opening polymerization to poly(2-alkyloxazoline)s. This type of polymers are under investigation as readily water-soluble and biocompatible materials for biomedical applications.


2-Ethyl-2-oxazoline, Production, From propionic acid and derivatives
Carboxylic acids, carboxylic esters, carboxylic amides and nitriles can react with 2-amino alcohols at 200 °C upon dehydration to the corresponding N-(2-hydroxy)carbamide, which react further at 260–280 °C upon dehydration to the 2-alkyl-2-oxazoline.


2-Ethyl-2-oxazoline, Production, From propionic acid and derivatives
For example N-(2-hydroxyethyl)propionamide is first formed from propionic acid and ethanolamine in 74% yield which can be dehydrated to give 2-ethyl-2-oxazoline in about 75% yield.


2-Ethyl-2-oxazoline, Production, From propionic acid and derivatives
Less drastic reaction conditions require the dehydration of the N-(2-hydroxyethyl)propionamide in vacuo in the presence of iron(III)chloride, which delivers the product in 90% yield. An even higher yield of 96.2% is obtained by heating with zinc acetate.


2-Ethyl-2-oxazoline, Production, From propionic acid and derivatives
An economic one-pot reaction is heating the salt of propionic acid with ethanolamine at 200 °C in vacuo in the presence of zinc chloride yielding 82% 2-ethyl-2-oxazoline. From the water-containing distillate pure 2-ethyl-2-oxazoline can be isolated by extraction with diethylbenzene and subsequent distillation or by distillation only after addition of diethyl phosphite or dimethyldichlorosilane. The product can be dried to a residual water content of 10 ppm.


2-Ethyl-2-oxazoline, Production, From propionic acid and derivatives
In another one-pot reaction propionic acid is converted first with 2-aminoethanol to 2-hydroxyethylamide, than reacted with boric acid at 130 °C yielding a boric acid ester which is finally thermolyzed at 280 °C in 92% yield to 2-ethyl-2-oxazoline.


2-Ethyl-2-oxazoline, Production, From propionic acid and derivatives
From propionic acid and thionyl chloride can be obtained propanoyl chloride, which reacts with ethanolamine in the  presence of an acid scavenger (for example pyridine) to  N-propionyl-2-aminoethanol. With further thionyl chloride this reacts further to 2-chloroethylamide. With the chloride ion as a better leaving group, this intermediate is cyclized by simple heating to the oxazoline. Water must be excluded du to the tendency of oxazolines towards ring-opening by chloride ions during protonation of the imine nitrogen.


2-Ethyl-2-oxazoline, Production, From propionic acid and derivatives
The direct reaction of propanoyl chloride with 2-chloroethylamine hydrochloride in the presence of triethylamine avoids the formation of water.


2-Ethyl-2-oxazoline, Production, From propanal
Propanal reacts with 2-aminoethanol in t-butanol to 2-ethyl-2-oxazoline in the presence of the iodinating reagent 1,3-diiodo-5,5-dimethylhydantoin (DIH) and potassium carbonate.


2-Ethyl-2-oxazoline, Properties
2-Ethyl-2-oxazoline is a readily water-soluble, colorless liquid which is also soluble in a variety of organic solvents and possesses an amine-like smell. Aqueous solutions react alkaline. The compound is stable in alkaline but hydrolyses under acid action.


2-Ethyl-2-oxazoline, Applications
In anhydrous form, 2-ethyl-2-oxazoline is mostly used as a monomer.


2-Ethyl-2-oxazoline, Applications
The cationic ring-opening polymerization of 2-ethyl-2-oxazoline can be initiated by alkylation with e.g. methyl tosylate or triflates (in particular methyl triflate) and leads to the water-soluble poly(2-ethyl-2-oxazoline) which is a propionyl-substituted linear polyethylenimine and can also be seen as a pseudo-polypeptide.


2-Ethyl-2-oxazoline, Applications
The polymerization of 2-ethyl-2-oxazoline can also be carried out as living cationic polymerization.


2-Ethyl-2-oxazoline, Applications
Copolymers with other 2-alkyl-2-oxazolines and other monomers allow the preparation of random copolymers and block copolymers.


2-Ethyl-2-oxazoline, Applications
The copolymers obtained can be used as biocompatible drug carriers, in coatings and adhesives, and in many other applications.


2-Ethyl-2-oxazoline, Applications
The elimination of the propionyl group from poly (2-ethyl-2-oxazoline) yields linear polyethyleneimine.


2-Ethyl-4,5-dimethylphenol
2-Ethyl-4,5-dimethylphenol is a phenol found in the essential oil of rosemary (Rosmarinus officinalis). It is also found in female elephant urine samples.


2-Ethylanthraquinone
2-Ethylanthraquinone is an organic compound that is a derivative of anthraquinone. This pale yellow solid is used in the industrial production of hydrogen peroxide (H2O2).


2-Ethylanthraquinone, Production
2-Ethylanthraquinone is prepared from the reaction of phthalic anhydride and ethylbenzene:


2-Ethylanthraquinone, Production
Both phthalic anhydride and ethylbenzene are readily available, being otherwise used in the large-scale production of plastics....


2-Ethylanthraquinone, Uses
Hydrogen peroxide is produced industrially by the anthraquinone process which involves using 2-alkyl-9,10-anthraquinones for hydrogenation. Many derivatives of anthraquinone are used but 2-ethylanthraquinone is common because of its high selectivity. The hydrogenation of the unsubstituted ring can reach 90% selectivity by using 2-ethylanthraquinone. Hydrogenation follows the Riedl-Pfleiderer, or autoxidation, process:


2-Ethylanthraquinone, Uses
The hydrogenation of 2-ethylanthraquinone is catalyzed by palladium. Hydrogenation produces both 2-ethylanthrahydroquinone and tetrahydroanthraquinone. The tetrahydro derivative of 2-alkylanthraquinone is easily hydrogenated but is more difficult to oxidize. The formation of the tetrahydro derivative can be suppressed through the selection of catalysts, solvents, and reaction conditions. Some suggested solvent mixtures are polyalkylated benzenes and alkyl phosphates or tetraalkyl ureas, trimethylbenzenes and alkylcyclohexanol esters, and methylnaphthalene and nonyl alcohols.


2-Ethylhexanoic acid
2-Ethylhexanoic acid is the organic compound with the formula CH3(CH2)3CH(C2H5)CO2H. It is a carboxylic acid that is widely used to prepare lipophilic metal derivatives that are soluble in nonpolar organic solvents. 2 -Ethylhexanoic acid is a colorless viscous oil. It is supplied as a racemic mixture.


2-Ethylhexanoic acid, Production
2-Ethylhexanoic acid is produced industrially from propylene, which is hydroformylated to give butyraldehyde. Aldol condensation of the aldehyde gives 2-ethylhexenal, which is hydrogenated to 2-ethylhexanal. Oxidation of this aldehyde gives the carboxylic acid.


2-Ethylhexanoic acid, Metal ethylhexanoates
2-Ethylhexanoic acid forms compounds with metal cations that have stoichiometry as metal acetates. These ethylhexanoate complexes are used in organic and industrial chemical synthesis. They function as catalysts in polymerizations as well as for oxidation reactions  as "oil drying agents." They are highly soluble in nonpolar solvents. These metal complexes are often described as salts. They are, however, not ionic but charge-neutral coordination complexes. Their structures are akin to the corresponding acetates.


2-Ethylhexanol
2-Ethylhexanol (abbreviated 2-EH) is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a massive scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers. It is encountered in plants, fruits, and wines. The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.


2-Ethylhexanol, Properties and applications
The branching in 2-ethylhexanol inhibits crystallization. Esters of 2-ethylhexanol are similarly affected, which together with low volatility, is the basis of applications in the production of plasticizers and lubricants, where its presence helps reduce viscosity and lower freezing points. Because 2-ethylhexanol is a fatty alcohol, its esters have emollient properties. Representative is the diester bis(2-ethylhexyl) phthalate (DEHP), commonly used in PVC. The triester tris (2-Ethylhexyl) trimellitate (TOTM) is another common plasticizer produced via the esterification of three 2-ethylhexanol per trimellitic acid.


2-Ethylhexanol, Properties and applications
It is also commonly used as a low volatility solvent. 2-Ethylhexanol can also be used as a cetane number booster when reacted with nitric acid. It also used to react with epichlorohydrin and sodium hydroxide to produce the glycidyl ether of the molecule which is used as an epoxy reactive diluent in various coatings, adhesives and sealants applications. It can be used in the development of photos, production of rubber and extraction of oil and gas.


2-Ethylhexanol, Industrial production
2-Ethylhexanol is produced industrially by the aldol condensation of n-butyraldehyde, followed by hydrogenation of the resulting hydroxyaldehyde. About 2,500,000 tons are prepared in this way annually.


2-Ethylhexanol, Industrial production
The n-butyraldehyde is made by hydroformylation of propylene, either in a self-contained plant or as the first step in a fully integrated facility. Most facilities make n-butanol and isobutanol in addition to 2-ethylhexanol. Alcohols prepared in this way are sometimes referred to as oxo alcohols. The overall process is very similar to that of the Guerbet reaction, by which it may also be produced.


2-Ethylhexanol, Health effects
2-Ethylhexanol exhibits low toxicity in animal models, with LD50 ranging from 2-3 g/kg (rat). 2-Ethylhexanol has been identified as a cause of indoor air quality related health problems, such as respiratory system irritation, as a volatile organic compound. 2-Ethylhexanol is emitted to air from a PVC flooring installed on concrete that had not been dried properly.


2-Ethylhexanol, Health effects
2-Ethylhexanol has been linked to developmental toxicity (increased incidence of skeletal malformations in fetuses). This is thought to be a result of metabolism of 2-ethylhexanol into 2-ethylhexanoic acid via oxidation of the primary alcohol. The teratogenicity of 2-ethylhexanoic acid, as well as similar substances such as valproic acid, has been well established.


2-Ethylhexanol, Nomenclature
Although isooctanol (and the derived isooctyl prefix) is commonly used in industry to refer to 2-ethylhexanol and its derivatives, IUPAC naming conventions dictate that this name is properly applied to another isomer of octanol, 6-methylheptan-1-ol. The Chemical Abstracts Service likewise indexes isooctanol (CAS# 26952-21-6) as 6-methylheptan-1-ol.


2-Ethylhexyl acrylate
2-Ethylhexyl acrylate is a colorless liquid acrylate with a unpleasant odor.


2-Ethylhexyl acrylate, Preparation
Racemic 2-ethylhexyl acrylate can be prepared with a high yield by esterification of acrylic acid with racemic 2-ethylhexanol in the presence of hydroquinone as a polymerization inhibitor and a strong acid such as methanesulfonic acid by reactive distillation using toluene as an azeotroping agent.


2-Ethylhexyl acrylate, Properties
2-Ethylhexyl acrylate polymerizes easily. The polymerization can be initiated by light, peroxides, heat, or contaminants. It can react violently when combined with strong oxidants and can form explosive mixtures with air at temperatures above 82 °C (180 °F). The chemical, physical, and toxicological properties, however, can be greatly modified by additives or stabilizers.


2-Ethylhexyl acrylate, Use
2-Ethylhexyl acrylate and butyl acrylate are the major base monomers for the preparation of acrylate adhesives. 2-Ethylhexyl acrylate can react by free-radical polymerization to form macromolecules having a molecular weight of up to 200,000 g/mol. Other monomers such as vinyl acetate, methyl acrylate, and styrene may be copolymerized to modify the properties of the resulting polymer.


2-Ethylhexyl diphenyl phosphate
2-Ethylhexyl diphenyl phosphate (Octicizer) is a plasticizer, flame retardant, and a main component of non-flammable hydraulic fluids. It has low acute toxicity in feeding experiments, but has been implicated as a potential hormone mimetic.


2-Fluoroamphetamine
2-Fluoroamphetamine (2-FA) is a stimulant drug from the amphetamine family which has been sold as a designer drug. 2-Fluoroamphetamine differs from 3- and 4-fluoroamphetamine in the position of the fluorine atom on the aromatic ring, making them positional isomers of one another. The replacement of a hydrogen atom with a fluorine atom in certain compounds to facilitate passage through the blood–brain barrier, as is desirable in central nervous system pharmaceutical agents, is a common practice due to the corresponding increase in lipophilicity granted by this substitution.


2-Fluoroamphetamine, Pharmacology
Anorexiant dose (amount inhibiting food intake by 50% for 2 hours, given 1 hour earlier) = 15 mg/kg (rat; p.o. ).


2-Fluoroamphetamine, Pharmacology
Analgesic dose (50% inhibition of response to tail-clamp) = 20 mg/kg (mouse; i.p. ).


2-Fluoroamphetamine, Pharmacology
Effect on blood pressure: 0.5 mg/kg (rat; i.v.) produces an increase in BP of 29 mm.


2-Fluoroamphetamine, Legal Status, United States
The Federal Analogue Act, 21 U.S.C. § 813, is a section of the United States Controlled Substances Act, allowing any chemical "substantially similar" to an illegal drug (in Schedule I or II) to be treated as if it were also in Schedule I or II, but only if it is intended (ref 1) for human consumption. 2-FA may be considered to be an analog of amphetamine, thus falling under the Federal Analog Act.


2-Fluoroamphetamine, Legal Status, China
As of October 2015 2-FA is a controlled substance in China.


2-Fluorobenzoic acid
2-Fluorobenzoic acid is an organic compound with the formula FC6H4CO2H. It is one of three isomeric fluorobenzoic acids. Its conjugate base is 2-fluorobenzoate. The compound is an irritant.


2-Fluorobenzoic acid
Its metabolism has been studied extensively in the field of microbiology. Its conjugate base is part of the pathway of 2-fluorobiphenyl metabolism by Pseudomonas pseudoalcaligenes.


2-Fluorodeschloroketamine
2-Fluorodeschloroketamine (also known as 2'-Fl-2-Oxo-PCM, Fluoroketamine and 2-FDCK) is a dissociative anesthetic  related to ketamine. Its sale and use as a designer drug has been reported in various countries. It is an analogue of ketamine where the chlorine group has been replaced by fluorine. Due to its recent emergence, the pharmocological specifics of the compound are mostly unclear.


2-Fluorodeschloroketamine, History
The synthesis of 2-FDCK was first described in a 2013 paper as part of a larger effort to synthesize and evaluate new anesthetic drugs based on ketamine and its analogues. Ketamine itself was first introduced in 1964 and was approved for clinical use in 1970. Since then it has become one of the most important and applicable general anesthetics as well as a popular recreational drug.


2-Fluorodeschloroketamine, History
The use of 2-FDCK as a designer drug has been reported in various countries. Many of these new psychoactive substances (NPS) appear on the drug market in order to circumvent existing drug policies. 2-FDCK was first formally notified by the EMCDDA in 2016, alongside 65 other new substances. Due to its recent appearance, little research has been done on the compound so far.


2-Fluorodeschloroketamine, Chemistry, Structure
2-FDCK belongs to a class of compounds called arylcyclohexylamines which contains various other drugs such as PCP and ketamine. Their general structure consists of a cyclohexylamine unit with an aryl group attached to the same carbon as the amine. 2-FDCK has an o-fluorophenyl group as an aryl substituent and the amine group is methylated. The cyclohexyl ring features a ketone group next to the amine position.


2-Fluorodeschloroketamine, Chemistry, Structure
The chemical structure of 2-FDCK differs from ketamine only in that there is a fluorine atom attached to the phenyl group. Ketamine has a chlorine atom in that position.


2-Fluorodeschloroketamine, Chemistry, Synthesis
2-FDCK can be synthesized in a five-step reaction process. First 2-fluorobenzonitrile reacts with the Grignard reagent cyclopentyl magnesium bromide followed by a bromination reaction to obtain α-bromocyclopentyl-(2-fluorophenyl)-ketone. The reaction of the obtained ketone with methylamine at -40 °C then results in the formation of α-hydroxycyclopentyl-(2-fluorophenyl)-N-methylamine. Finally, the five-membered ring cyclopentanol form is expanded to a cyclohexylketone form by a thermal rearrangement reaction. HCl is used to create a water-soluble HCl salt of 2-FDCK.


2-Fluorodeschloroketamine, Chemistry, Detection
2-FDCK and its metabolites can be detected in urine with the use of liquid chromatography mass spectrometry (LC/MS).


2-Fluorodeschloroketamine, Pharmacology, Metabolism
The metabolism of 2-FDCK is analogous to that of ketamine: the enzymes CYP2B6 and CYP3A4, the latter to a lesser extent, metabolise 2-FDCK to Nor-2FDCK via N-demethylation. This is further metabolised either to dehydronor-2FDCK by CYP2B6 or to hydroxynor-2FDCK by CYP2A6 and CYP2B6.


2-Fluorodeschloroketamine, Pharmacology, Metabolism
In general, the 2-FDCK equivalent shows stronger docking to CYP2B6 in simulations, as well as slower metabolism rate, than the more well-known Ketamine. The lipophilicity is observed to be lower for 2-FDCK than for Ketamine. In vitro to in vivo extrapolation (IVIVE) predicts that in the body, 2-FDCK shows a lower intrinsic hepatic clearance than ketamine. Both of these characteristics would suggest that the effects of 2-FDCK last longer than those of ketamine.


2-Fluorodeschloroketamine, Pharmacology, Pharmacodynamics
2-FDCK is structurally similar to ketamine, so a similar mechanism of action is expected, but there has been no study done to confirm this. Due to the halogen in the 2 position not being a chlorine but a fluorine, the molecule is less polar. This could influence binding to proteins, such as the NMDA receptor that ketamine primarily binds to and acts as an antagonist towards.


2-Fluorodeschloroketamine, Pharmacology, Pharmacodynamics, Comparison to other halogen-substituted ketamine variants
For general (halogen) substitutions of ketamine, docking strength for CYP2B6 follows the pattern H < Br < Cl < F. The parameter of internal clearance follows the pattern Br > Cl > F > H. Lastly, Km (Michaelis constant) follows the pattern of Br < Cl < F < H, and as such the in-vitro metabolism rate follows the inverse pattern, namely Br > Cl > F > H.


2-Fluorodeschloroketamine, Effects, Dosage
2-FDCK is very new and not yet sufficiently studied. Therefore information on dosage can only be obtained from purely anecdotal sources.


2-Fluorodeschloroketamine, Effects, Possible effects and dangers
In 2019, 2-FDCK was found in poisoned individuals in Hong Kong in combination with other ketamine-type drugs. 2-FDCK was not assumed to be an impurity because it was present in high levels while ketamine was present at trace levels. The actual drug specimens were not available, so it was not possible to verify this. Clinical effects were observed but because the drug was taken in combination with other ones, it was not possible to determine what effects were caused by which drug. The clinically observed effects of the patients were: impaired consciousness, agitation, abnormal behaviour, hypertension and tachycardia. Most patients were discharged from the hospital after a few days of supportive treatment.


2-Fluorodeschloroketamine, Legal status
Due to the fast emergence of NPS, new substances such as 2-FDCK are often not yet specifically mentioned in controlled substance legislation. As a result, NPS are sometimes marketed as 'legal highs'. 2-FDCK is currently illegal in Italy Japan, Latvia, Singapore, Sweden, Switzerland, as well as being covered by blanket bans in Canada, Belgium, and the UK.


2-Fluoroethanol
2-Fluoroethanol is the organic compound with the formula CH2FCH2OH. This colorless liquid is one of the simplest stable fluorinated alcohols. It was once used as a pesticide. The related difluoro- and trifluoroethanols are far less dangerous.


2-Fluoroethanol, Synthesis
2-Fluoroethanol was originally synthesized by treating 2-chloroethanol with potassium fluoride, in a simple Finkelstein reaction. The product has a lower boiling point that the starting material and may be conveniently isolated by distillation.


2-Fluoroethanol, Structure and reactivity
Reaction of 2-fluoroethanol with  trifluoromethanesulfonic anhydride in the presence of base gives the triflate ester.


2-Fluoroethanol, PET radiotracers
2-[18F]-fluoroethoxy group is a common moiety in the structures of radiotracers used with PET. Such radiotracers include fluoroethyl-l-tyrosine 1-(2-[18F]-fluoroethoxy)-4-nitrobenzene and [18F]-fluoroethyl 4-fluorobenzoate, being a [18F]fluoroalkyl ether and ester respectively.


2-Fluoroethanol, Metabolism
It was patented as a rodenticide in Germany in 1935. In rats, it was found that fluoroethanol induced a similar toxicity as that of fluoroacetate, known to metabolize to fluorocitrate to exert the toxic effect.


2-Fluoroethanol, Metabolism
2-Fluoroethanol is converted by alcohol dehydrogenase (ADH) using nicotinamide adenine dinucleotide (NAD+) as cofactor, ultimately leading to the formation of fluoroacetaldehyde and then fluoroacetate.


2-Fluoroethanol, Metabolism
Fluoroacetate is a precursor to fluorocitrate, an inhibitor of aconitase, an enzyme that participates in the TCA cycle.


2-Fluoroethanol, Toxicity
Reported effects of 2-fluoroethanol are epigastric distress effects, such as vomiting, and central nervous effects, such as auditory hallucinations, numbness feeling of the face or nose. Both these types of effects occur gradually after being exposed to 2-fluoroethanol for several hours. Some more severe reactions of the human body to 2-fluoroethanol can be respiratory failure  and epileptiform convulsions or seizures, leading to dysfunctions in the heart mechanism. From the late 20th century, there are multiple reports of deaths caused by 2-fluoroethanol.


2-Fluoroethanol, Toxicity
2-Fluoroethanol is also toxic to other animals with LD50 ranging from 7 to 1500 mg/kg bodyweight.


2-Fluoromethamphetamine
2-Fluoromethamphetamine (2-FMA) is a stimulant drug of the amphetamine family which has been used as a designer drug . It is purported to possess little recreational value because less euphoria is produced than other amphetamines. It is said to be a functional stimulant with properties similar to lisdexamfetamine. It lasts about 8 hours orally, considerably more than its analogue 2-FA.


2-Fluoromethamphetamine, Legal status, China
As of October 2015, 2-FMA is a controlled substance in China.


2-Fluoromethamphetamine, Legal status, Ukraine
As of July 2019, 2-FMA is a controlled substance in Ukraine (considered a narcotic).


2-Formylbenzoate dehydrogenase
2-Formylbenzoate dehydrogenase (EC , 2-carboxybenzaldehyde dehydrogenase, 2CBAL dehydrogenase, PhdK) is an enzyme with systematic name 2-formylbenzoate:NAD+ oxidoreductase. This enzyme catalyses the following chemical reaction


2-Furanone
2-Furanone is a heterocyclic organic compound. It is also known as γ-crotonolactone (GCL), as it is formally the lactone derived from γ-hydroxyisocrotonic acid. The chemical is colloquially called "butenolide", and is the parent structure for the butenolide class of compounds. It is a colourless liquid.


2-Furanone, Synthesis and reactions
It exists in equilibrium with the tautomer 2-hydroxyfuran, which serves as an intermediate in the interconversion between the β- and α-furanones. The β form is the more stable. The interconversion is catalyzed by base.


2-Furanone, Synthesis and reactions
2-Furanones can be converted to furans by a two-step process of reduction followed by dehydration.


2-Furoic acid
2-Furoic acid is a heterocyclic carboxylic acid, consisting of a five-membered aromatic ring and a carboxylic acid group. Its name is derived from the Latin word furfur, meaning bran. The salts and esters of furoic acids are known as furoates.


2-Furoic acid
2-Furoic acid is an organic compound most widely found in food products as a preservative and a flavoring agent. Other uses for 2-furoic acid include nylon preparation and optic technologies.


2-Furoic acid, History
The molecule first described by Carl Wilhelm Scheele in 1780 and was the first known derivative of the heterocycle known as furan. Since then, the compound's reactivity with different substances and organisms was tested. It was discovered that 2-furoic acid can be the sole source of carbon and energy for the organism Pseudomonas putida. The organism aerobically degrades the compound.


2-Furoic acid, Preparation and synthesis
2-Furoic acid can be synthesized by the oxidation of either furfuryl alcohol or furfural. This can be achieved either chemically or biocatalytically. Currently the industrial route involves the Cannizaro reaction of furfural in an aqueous NaOH solution; this route produces both 2-furoic acid and furfuryl alcohol. The bio-catalytic route involves the microorganism Nocardia corallina. Experiments involving this microbial conversion resulted in high yields: 98% from 2-furfuryl alcohol and 88% from 2-furanaldehyde. Oxidation with N. corallina is unique because most other microorganisms produce two products from the oxidation, the acid and the alcohol. Furthermore, aromatic ring destruction does not occur.


2-Furoic acid, Applications and occurrences
In industrial use, 2-furoic acid is a preservative, acting as a bactericide and fungicide. It is also considered an acceptable flavoring ingredient and achieved a generally recognized as safe (GRAS) status in 1995 by the Flavor and Extract Manufacturers Association (FEMA). 2-Furoic acid is characterized as a white to off-white crystalline solid and has a distinct odor described in the Encyclopedia of Food and Color Additives as sweet, oily, herbaceous, and earthy. 2-Furoic acid is often used as a starting material for the production of furoate esters. It and its derivatives also aid in the production of nylons, and are often used in biomedical research.


2-Furoic acid, Reactions
For the most part 2-furoic acid is relatively stable. However, 2-furoic acid is reactive with oxidizing materials. It is not reactive with reducing agents, combustible materials, organic materials, metals, acids, or alkalis.


2-Furoic acid, Importance in optic technology
2-furoic acid may have an important role in the field of optic technology. Studies concerning the preparation of 2-furoic acid crystals have shown indication of several favorable properties of non-linear optical materials (NLOs). These crystals are highly transparent in the 200–2000 nm, wavelength region, are stable up to 130 °C, and generally have low absorption in the UV, visible, and IR spectrums. In optical and dielectric studies, 2-furoic acid crystals have been shown to have decreasing dielectric constants with increasing frequencies.


2-Furoic acid, Importance in optic technology
This could mean that the crystals may act as paraelectrics in the temperature range before 318 K and ferroelectrics in temperature ranges after 318 K. These qualities indicate that 2-furoic acid crystals will have enhanced optical quality with less defects, which is important in the application of optical devices. Depending on the process of crystal formation, the surface of the grown crystals is generally smooth, with occasional microcrystals on the surface.


2-Furoic acid, 2-Furoic acid in foods
2-furoic acid helps sterilize and pasteurize many foods. The main mechanism that produces the 2-furoic acid for food sterilization is known as the Cannizzaro reaction of 2-furfural. 2-furoic acid is also formed during coffee roasting, with up to 205 mg/kg.


2-Furoic acid, Hazards
Research on the effects of 2-furoic acid in rats showed an increase in bile salts and acute toxicity suggesting potential toxic effects. 2-Furoic acid may also cause mutagenic effects in bacteria and yeasts, leading to damage and irritation to the gastrointestinal tract, respiratory tract, skin, and eyes.


2-Furonitrile
2-Furonitrile is a colorless derivative of furan possessing a nitrile group.


2-Furonitrile, Synthesis
Industrial synthesis is based on the vapor phase ammoxidation of furfural with ammonia over bismuth molybdate catalyst at 440-480 °C.


2-Furonitrile, Synthesis
Numerous laboratory methods also exist; for the instance oxidative dehydration of furfural with ammonia salts using hypervalent iodine reagents or n-bromosuccinimide. From furfural aldoxime (with thionyl chloride-benzotriazole, triphenylphosphine-iodine reagents, or heating in DMSO) and furoic acid amide (flash vacuum pyrolysis).


2-Furonitrile, Applications
2-Furonitrile currently has no major applications but it is used as an intermediate in pharmaceutical and fine chemical synthesis. It has been suggested as a potential sweetening agent, as it has about thirty times the sweetening power of sucrose.


2-Furoyl chloride
2-Furoyl chloride is an acyl chloride of furan. It takes the form of a corrosive liquid, which is more irritating to the eyes than benzoyl chloride. 2-Furoyl chloride is a useful pharmaceutical intermediate and is used in the synthesis of mometasone furoate, an antiinflammatory prodrug used in the treatment of skin disorders, hay fever and asthma.


2-Furoyl chloride, Synthesis
2-Furoyl chloride was prepared in 1924 by Gelissen by refluxing 2-furoic acid in excess thionyl chloride on a water bath.


2-Furoyl chloride, Applications
2-Furoyl chloride has no major applications but it has been used as a chemical intermediate in the synthesis of various pharmaceuticals; examples include mometasone furoate, fluticasone furoate, diloxanide furoate, Ceftiofur (Excenel), mirfentanil, quinfamide, and diclofurime.


2-Headed Shark Attack
2-Headed Shark Attack is an American low-budget survival horror film with an ensemble cast by The Asylum, released on January 31, 2012 in the United States. Directed by Christopher Ray, the film stars Carmen Electra, Charlie O'Connell, Brooke Hogan, Christina Bach, David Gallegos and Corinne Nobili. The film premiered on September 8, 2012 on Syfy.


2-Headed Shark Attack, Plot
The film opens with a group of wakeboarders being attacked and devoured by a two-headed great white shark. Meanwhile, Sea King, a Semester at Sea ship led by Professor Franklin Babish (Charlie O'Connell) and his wife, Anne (Carmen Electra), hits a dead shark. The shark becomes lodged in the boat's propeller, damaging the ship's hull and causing the boat to take on water. Soon after, the two-headed shark attacks the boat and breaks the radio antenna, preventing ship co-captain Laura from summoning help. Professor Babish and the students use a dinghy to take shelter on a nearby deserted atoll, while Anne remains on the Sea King with Laura and the ship's crew, Han and Dikilla. Laura enters the water to repair the ship's hull, and is quickly ripped apart by the two-headed shark.


2-Headed Shark Attack, Plot
Meanwhile, professor and the students explore the atoll. Assembling in an abandoned fishing village, they set out to search the atoll for scrap metal to help repair the boat. Haley and Alison decide to go swimming topless with Kirk, only to be attacked and eaten by the two-headed shark. The rest of the group meet up and find two small speedboats before an earthquake hits, causing Professor Babish to fall and badly injure his leg. Dana bandages Babish's leg with her shirt, while Jeff and Mike accompany him back to the Sea King on the dinghy. On the way back, Jeff and Mike discover Laura's severed hand in the water. They are attacked by the shark and eaten while attempting to swim back to the Sea King.


2-Headed Shark Attack, Plot
The students find two boats on the island, which Kate (Brooke Hogan) and Paul manage to fix. Cole finds a gasoline tank to fuel them, but then steals one together with Ryan, Jamie and Alex. Kate, Paul and Dana follow them in the other boat. They are all unaware of the shark, which attacks Cole's boat. Ryan falls into the water and is eaten, alerting the others to the shark's presence. Paul concludes the shark is drawn to Cole's boat as it has a bigger engine. Cole also deduces this and bails; the shark eats Jamie and Alex. When the survivors reach shore, Kate furiously confronts Cole for his actions. A few minutes later, the Sea King is abandoned and the survivors meet on the island.


2-Headed Shark Attack, Plot
Shortly afterward, another earthquake hits. The group realizes that the earthquakes are actually caused by the atoll collapsing in on itself. Escape being ever more urgent, the group hooks up a generator to metal poles and places them in the water to distract the shark with electricity while Kate and Cole travel to the Sea King and repair the hull. The plan works until the shark attacks the poles, knocking Han and Dikilla into the water to their deaths. Kate fixes the ship, only for Cole to drive away without her, forcing her to swim back to the atoll. The two-headed shark attacks the Sea King, causing it to sink and send out a distress signal; Cole is then eaten trying to escape on a lifeboat when his cellphone alerts the shark. The atoll is sinking too, prompting everyone to flee for their lives.


2-Headed Shark Attack, Plot
Dana and Kristen get separated from the group and are quickly devoured. Professor Babish and Anne also get separated from the group, and after running into a dead-end due to a tsunami suddenly approaching the atoll, they share one final kiss as the shark eats them both. The rest of the group end up in or near the water as the small tsunami strikes the island. The remaining students swim into the half-sunk village chapel to hide, but the shark breaks in.


2-Headed Shark Attack, Plot
Lyndsey uses a gun she found to try and shoot the shark, but it does nothing and the shark quickly rips her apart. Ethan uses the giant wooden cross in the chapel to try attacking the shark, which also does no good as it then devours both Liza and Michelle. Paul, Kate, and Kirsten all climb out the window and escape while Ethan distracts the shark, only for him to get caught and eaten as well.


2-Headed Shark Attack, Plot
The final three discover a gasoline tank, and lure the shark towards it. Kate attempts to stab the shark and is nearly eaten, but Kirsten sacrifices herself instead to try to blow up the shark. As it eats and kills her, she manages to light a fuse and cause an explosion. However, only one of the shark's heads get blown off. Kate and Paul find one of the boats and turn it on as a decoy, taking shelter on part of the remaining atoll still above water. The shark attacks the unmanned boat. It bites the motor, which explodes, finally killing the shark (a homage to Jaws). A helicopter arrives, having been summoned from the distress signal sent out from the sunken Sea King, saving Kate and Paul, leaving only two survivors out of 23 people.


2-Headed Shark Attack, Production
The design for the 2-headed shark was detailed in the Monster Man episode "Seeing Double". The original design of the shark had one shark head stacked on top of the other. However, creature designer Cleve Hall pushed to change the design to side-by-side heads.


2-Headed Shark Attack, Production, Release
The film saw release on DVD with special features including a gag reel in 2012  and on Blu-ray including a "Making of" special feature.


2-Headed Shark Attack, Soundtrack
The film features "More" and "Swallow Whole" by Neon Line. "It's Killing Me to Live" by Matthew Arner. "Jungle Jam" by Yoshi Miyamoto. As well as "Transmission" by Closer to Venus.


2-Headed Shark Attack, Reception
Bloody Disgusting published a review of the film in 2017, arguing that the film attempts to develop some of the extensive list of characters and puts "makes an effort to give them all unique personalities and character traits, even if there simply isn't enough time devoted to developing them". The review commends the film for also delivering on the titular "2-headed shark attack", but argues that "the over-the-top massacres are good fun at first, but do get stale after a while" and that the film could have benefitted from cutting some characters and making the remaining death scenes more creative.


2-Headed Shark Attack, Sequels
A sequel, 3-Headed Shark Attack, was produced in 2015 by The Asylum and directed by Christopher Ray. The film features Jaason Simmons, Danny Trejo, and wrestler Rob Van Dam in leading roles. The plot revolves around marine biology students encountering a three-headed shark.


2-Headed Shark Attack, Sequels
Two more films in the series premiered on Syfy, 5-Headed Shark Attack on July 30, 2017 and 6-Headed Shark Attack on August 18, 2018. A fifth film, 7-Headed Shark Attack, is planned.


2-Heptanol
2-Heptanol is a chemical compound which is an isomer of heptanol. It is a secondary alcohol with the hydroxyl on the second carbon of the straight seven-carbon chain.


2-Heptanone
2-Heptanone, also known as methyl n-amyl ketone, or Heptan-2-one, is a ketone with the molecular formula C7H14O. It is a colorless, water-like liquid with a banana-like, fruity odor. 2-Heptanone has a neutral formal charge, and is only slightly soluble in water.


2-Heptanone
2-Heptanone is listed by the FDA as a "food additive permitted for direct addition to food for human consumption" (21 CFR 172.515), and it occurs naturally in certain foods (e.g., beer, white bread, butter, various cheeses and potato chips).


2-Heptanone
The mechanism of action of 2-heptanone as a pheromone at odorant receptors in rodents has been investigated. 2-Heptanone is present in the urine of stressed rats and believe that it is used as a means to alert other rats. Certain species of worms are attracted to 2-heptanone and bacteria can use this as a means of pathogenesis. 2-Heptanone has also been found to be excreted by honey bees when they bite small pests within the colony such as wax moth larvae and Varroa mites.


2-Heptanone
Though it was historically believed to be an alarm pheromone, 2-heptanone has been shown to act as an anaesthetic on the pests, enabling the honey bee to stun the pest and eject it from the hive. The work could lead to the use of 2-heptanone as an alternative local anaesthetic to lidocaine, which although well established for clinical use, has the disadvantage of provoking allergic reactions in some people.


2-Heptanone
2-Heptanone was one of the metabolites of n-heptane found in the urine of employees exposed to heptane in shoe and tire factories. This commonly occurs from exposure to plasticisers. 2-Heptanone can be absorbed through the skin, inhaled and consumed. Exposure to 2-Heptanone can cause irritation of skin/eyes, respiratory system, headaches, vomiting, and nausea.


2-Hexanol
2-Hexanol (or hexan-2-ol) is a six carbon alcohol in which the OH group is located on the second carbon atom. Its chemical formula is C6H14O or C6H13OH. It is an isomer of the other hexanols. 2-Hexanol has a chiral center and can be resolved into two different enantiomers.


2-Hexanone
2-Hexanone (methyl butyl ketone, MBK) is a ketone used as a general solvent and in paints. It dissolves cellulose nitrate, vinyl polymers and copolymers, and natural and synthetic resins. It is recommended as a solvent because it is photochemically inactive; however it has a very low safe threshold limit value. 2-Hexanone is absorbed through the lungs, orally and dermally and its metabolite, 2,5-hexanedione, is neurotoxic. Animal tests have shown that the neurotoxic effect of 2-hexanone may be potentiated by simultaneous administration of 2-butanone (methyl ethyl ketone, MEK).


2-Hexoxyethanol
2-Hexoxyethanol or 2-(Hexyloxy)ethanol is a glycol ether that has a chemical formula of C8H18O2.


2-Hexoxyethanol, Uses
2-Hexoxyethanol is used by professional workers (widespread uses), consumers, in re-packing or re-formulation,  in manufacturing, and at industrial sites. It is used as high-boiling solvent. It also serves as an intermediate for neopentanoate and hexyloxyethyl phosphate. It serves as a coalescing agent in cleaners and latex paints.


2-Hexoxyethanol, Hazards
According to the European Chemicals Agency, it is classified as harmful when in contact with skin and when swallowed. It can also skin burns and serious eye damage.


2-Hexoxyethanol, Hazards
2-Hexoxyethanol was also known to cause kidney injury and depression. It is also a severe respiratory tract irritant. It may also have blood effects. It may enter the body through ingestion, aerosol inhalation, and through the skin.


2-Hexoxyethanol, Hazards
It may form explosive peroxides. It can react violently with strong oxidants.


2-Hexoxyethanol, Hazards
It is classified as a green circle product EPA Safer Choice meaning it is of low concern.


2-Hexyne
2-Hexyne is an organic compound that belongs to the alkyne group. Just like its isomers, it also has the chemical formula of C6H10.


2-Hexyne, Reactions
2-Hexyne can be semihydrogenated to yield 2-hexene or fully hydrogenated to hexane. With appropriate noble metal catalysts it can selectively form cis-2-hexene.


2-Hexyne, Reactions
With strong sulfuric acid, the ketone 2-hexanone is produced. However this reaction also causes polymerization and charring.


2-Hexyne, Reactions
Under heat and pressure 2-hexyne polymerizes to linear oligomers and polymers. This can be hastened by some catalysts such as molybdenum pentachloride with tetraphenyl tin. However Ziegler–Natta catalysts have no action as the triple bond is hindered.


2-Hydroxy-1,4-benzoxazin-3-one monooxygenase
2-Hydroxy-1,4-benzoxazin-3-one monooxygenase (EC , BX5 (gene), CYP71C3 (gene)) is an enzyme with systematic name 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one,NAD(P)H:oxygen oxidoreductase (N-hydroxylating). This enzyme catalyses the following chemical reaction


2-Hydroxy-1,4-benzoxazin-3-one monooxygenase
2-Hydroxy-1,4-benzoxazin-3-one monooxygenase is involved in the biosynthesis of protective and allelopathic benzoxazinoids in some plants.


2-Hydroxy-3-methyl-2-cyclopenten-1-one
2-Hydroxy-3-methyl-2-cyclopenten-1-one  is an organic compound related to 1,2-cyclopentanedione. It is the enol tautomer of the diketone 3-methylcyclopentane-1,2-dione. Being an enol, the compound is often called methylcyclopentenolone. It is a colorless solid.


2-Hydroxy-3-methyl-2-cyclopenten-1-one, Synthesis and structure
The compound is prepared by base-catalyzed condensation of 1‐hydroxyhexane‐2,5‐dione, a derivative of hydroxymethylfurfural.


2-Hydroxy-3-methyl-2-cyclopenten-1-one, Synthesis and structure
The structure has been confirmed by X-ray crystallography. Quantum calculations also indicate that the enol is strongly favored relative to the diketo tautomer. Furthermore, the enolization occurs at the methyl-substituted carbon.


2-Hydroxy-3-methyl-2-cyclopenten-1-one, Use and occurrence
It is one of many products from the pyrolysis of lignocellulose.


2-Hydroxy-3-methyl-2-cyclopenten-1-one, Use and occurrence
It is used in flavors and perfumery for its maple- or caramel-like odor. It contributes to the flavor or odor of many foods including wines, coffee, paprika, and salmon. It is sometimes called maple lactone because it occurs in maple syrup (it is not, however, a lactone).


2-Hydroxy-3-morpholinopropanesulfonic acid
MOPSO is a zwitterionic organic chemical buffering agent; one of Good's buffers. MOPSO and MOPS (3-morpholinopropanesulfonic acid) are chemically similar, differing only in the presence of a hydroxyl group on the C-2 of the propane moiety. It has a useful pH range of 6.5-7.9 in the physiological range, making it useful for cell culture work. It has a pKa of 6.9 with ΔpKa/°C of -0.015 and a solubility in water at 0°C of 0.75 M.


2-Hydroxy-4-methoxybenzaldehyde
2-Hydroxy-4-methoxybenzaldehyde is a chemical compound and an isomer of vanillin. Urolithin M7, one of the urolithins, has also been synthesized from 2-hydroxy-4-methoxybenzaldehyde using the inverse electron-demand Diels–Alder reaction.


2-Hydroxy-4-methylbenzaldehyde
2-Hydroxy-4-methylbenzaldehyde is a chemical compound. It is an additives in cigarettes.


2-Hydroxy-5-methoxybenzaldehyde
2-Hydroxy-5-methoxybenzaldehyde is an organic compound and an isomer of vanillin.


2-Hydroxy-5-methoxybenzaldehyde, Synthesis and reactions
The chemical is produced by the Reimer-Tiemann reaction on 4-methoxyphenol with a 79% yield.


2-Hydroxy-5-methoxybenzaldehyde, Synthesis and reactions
It reacts with malononitrile to form 2-imino-6-methoxy-2H-1-benzopyran-3-carbonitrile. It can be reduced by sodium borohydride in ethanol to form 2-hydroxy-5-methoxybenzyl alcohol.


2-Hydroxyacylsphingosine 1-beta-galactosyltransferase
In enzymology, a 2-hydroxyacylsphingosine 1-beta-galactosyltransferase (EC ) is an enzyme that catalyzes the chemical reaction


2-Hydroxyacylsphingosine 1-beta-galactosyltransferase
Thus, the two substrates of this enzyme are UDP-galactose and 2-(2-hydroxyacyl)sphingosine, whereas its two products are UDP and 1-(beta-D-galactosyl)-2-(2-hydroxyacyl)sphingosine.


2-Hydroxyacylsphingosine 1-beta-galactosyltransferase
This enzyme belongs to the family of glycosyltransferases, specifically the hexosyltransferases. The systematic name of this enzyme class is UDP-galactose:2-(2-hydroxyacyl)sphingosine 1-beta-D-galactosyl-transferase. Other names in common use include galactoceramide synthase, uridine diphosphogalactose-2-hydroxyacylsphingosine, galactosyltransferase, UDPgalactose-2-hydroxyacylsphingosine galactosyltransferase, UDP-galactose:ceramide galactosyltransferase, and UDP-galactose:2-2-hydroxyacylsphingosine galactosyltransferase.


2-Hydroxybutyric acid
2-Hydroxybutyric acid, also known as alpha-hydroxybutyrate and α-hydroxybutyrate, is a hydroxybutyric acid with the hydroxyl group on the carbon adjacent to the carboxyl. It is a chiral compound having two enantiomers, D-2-hydroxybutyric acid and L-2-hydroxybutyric acid.


2-Hydroxybutyric acid
2-Hydroxybutyrate, the conjugate base of 2-hydroxybutyric acid, is produced in mammalian tissues (principally hepatic) that catabolize L-threonine or synthesize glutathione. Oxidative stress or detoxification demands can dramatically increase the rate of hepatic glutathione synthesis. Under such metabolic stress conditions, supplies of L-cysteine for glutathione synthesis become limiting, so homocysteine is diverted from the transmethylation pathway forming methionine into the transsulfuration pathway forming cystathionine. 2 -Hydroxybutyrate is released as a byproduct when cystathionine is cleaved to cysteine that is incorporated into glutathione. Chronic shifts in the rate of glutathione synthesis may be reflected by urinary excretion of 2-hydroxybutyrate.


2-Hydroxybutyric acid
α-hydroxybutyrate may be useful as an early indicator of insulin resistance in non-diabetic subjects. Moreover, elevated serum α-hydroxybutyrate predicts worsening glucose tolerance.


2-Hydroxyestradiol
2-Hydroxyestradiol (2-OHE2), also known as estra-1,3,5(10)-triene-2,3,17β-triol, is an endogenous steroid, catechol estrogen, and metabolite of estradiol, as well as a positional isomer of estriol.


2-Hydroxyestradiol, Biosynthesis
Transformation of estradiol to 2-hydroxyestradiol is a major metabolic pathway of estradiol in the liver. CYP1A2 and CYP3A4 are the major enzymes catalyzing the 2-hydroxylation of estradiol. Conversion of estradiol into 2-hydroxyestradiol has also been detected in the uterus, breast, kidney, brain, and pituitary gland, as well as the placenta, and may similarly be mediated by cytochrome P450 enzymes. Although estradiol is extensively converted into 2-hydroxyestradiol, circulating levels of 2-hydroxyestradiol and levels of 2-hydroxyestradiol in various tissues are very low. This may be due to rapid conjugation (O-methylation, glucuronidation, sulfonation) of 2-hydroxyestradiol followed by urinary excretion.


2-Hydroxyestradiol, Biological activity, Estrogenic activity
2-Hydroxyestradiol has approximately 7% and 11% of the affinity of estradiol at the estrogen receptors (ERs) ERα and ERβ, respectively. It dissociates from the estrogen receptors more rapidly than does estradiol. The steroid is only very weakly estrogenic, and is able to antagonize the estrogenic effects of estradiol, indicating that its intrinsic activity at the estrogen receptor is less than that of estradiol and hence that it possesses the profile of a selective estrogen receptor modulator. It shows estrogenic activity in human breast cancer cells. In addition to its activity at the nuclear ERs, 2-hydroxyestradiol is an antagonist of the G protein-coupled estrogen receptor (GPER) (100–1,000 μM).


2-Hydroxyestradiol, Biological activity, Catecholaminergic activity
2-Hydroxyestradiol is a catechol estrogen and in this regard bears some structural resemblance to the catecholamines dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline). In accordance, 2-hydroxyestradiol has been found to interact with catecholamine systems. The steroid is known to compete with catecholamines for binding to catechol O-methyltransferase and tyrosine hydroxylase and to directly and competitively inhibit these enzymes. In addition, 2-hydroxyestradiol has been found to displace spiperone from the D2 receptor with approximately 50% of the affinity of dopamine, whereas estradiol, estrone, and estriol and their other 2-hydroxylated and 2-methoxylated derivatives showed only weak or negligible inhibition. Moreover, 2-hydroxyestradiol has been found to bind to the α1-adrenergic receptor with slightly more than half the affinity of norepinephrine. However, although these affinities are comparable to those of dopamine and norepinephrine, they are nonetheless in the double-digit micromolar range.


2-Hydroxyestradiol, Biological activity, Catecholaminergic activity
2-Hydroxyestradiol has been found to increase prolactin secretion when administered intravenously to women. It was noted that this could be due to 2-hydroxyestradiol binding to and antagonizing the D2 receptor. However, the researchers argued against this possibility because it was delayed (by several hours) and of relatively small magnitude, whereas established D2 receptor antagonists promptly induce marked increases in prolactin levels. The researchers also argued against the possibility that it was due to inhibition of dopamine biosynthesis by 2-hydroxyestradiol because 2-hydroxyestrone, which inhibits tyrosine hydroxylase similarly to 2-hydroxyestradiol, showed no such increase in prolactin secretion. The researchers concluded that the most likely explanation was that the increase was mediated by the estrogenic activity of 2-hydroxyestradiol, as similar increments in prolactin levels had been observed with estradiol. In any case, these findings argue against the notion of major interactions of 2-hydroxyestradiol with the dopamine system.


2-Hydroxyestradiol, Biological activity, Genotoxicity
2-Hydroxyestradiol, as well as 2-hydroxyestrone and 4-hydroxyestradiol, can undergo metabolic redox cycling to generate free radicals like superoxide and reactive estrogen semiquinone/quinone intermediates. These metabolites may damage DNA and other cellular components. However, 2-hydroxyestradiol shows little or no tumorigenic activity in the male Syrian hamster kidney and there is evidence that 2-hydroxyestradiol may actually decrease tumorigenesis in estrogen-sensitive tissues. It has been suggested that the lack of tumorigenesis of 2-hydroxyestrone is due to its rapid clearance. In addition, its metabolite 2-methoxyestradiol is a very potent inhibitor of tumor growth and angiogenesis, and this may contribute as well.


2-Hydroxyestradiol, Biological activity, Production of 2-methoxyestradiol
2-Hydroxyestradiol has been identified as a prodrug of 2-methoxyestradiol, a transformation which is very efficiently catalyzed by catechol O-methyltransferase in the liver. 2-Methoxyestradiol is not estrogenic but is a potent angiogenesis inhibitor and agonist of the GPER with potential therapeutic implications in cancer.


2-Hydroxyestradiol, Biological activity, Antioxidant activity
Similarly to other steroidal estrogens, 2-hydroxyestradiol is an antioxidant, but the catechol estrogens (2- and 4-hydroxylated estrogens) like 2-hydroxyestradiol are considered to be the most potent in terms of antioxidant activity.


2-Hydroxyestradiol, History
2-Hydroxyestradiol was identified as a metabolite of estradiol in 1960.


2-Hydroxyestriol
2-Hydroxyestriol, also known as estra-1,3,5(10)-triene-2,3,16α,17β-tetrol, is an endogenous catechol estrogen and metabolite of estriol. It is a suspected carcinogen of carcinogenicity category 2.


2-Hydroxyestrone
2-Hydroxyestrone (2-OHE1), also known as estra-1,3,5(10)-trien-2,3-diol-17-one, is an endogenous, naturally occurring catechol estrogen and a major metabolite of estrone and estradiol. It is formed irreversibly from estrone in the liver and to a lesser extent in other tissues via 2-hydroxylation mediated by cytochrome P450 enzymes, mainly the CYP3A and CYP1A subfamilies. 2-OHE1 is the most abundant catechol estrogen in the body.


2-Hydroxyestrone
2-Hydroxyestrone is not significantly uterotrophic in bioassays, whereas other hydroxylated estrogen metabolites including 2-hydroxyestradiol, 16α-hydroxyestrone, estriol (16α-hydroxyestradiol), 4-hydroxyestradiol, and 4-hydroxyestrone all are. In addition, although not antiestrogenic in the uterus, 2-hydroxyestrone shows antiestrogenic effects on luteinizing hormone and prolactin levels. The lack of estrogenic or antiestrogenic activity of 2-hydroxyestrone in the uterus may be attributable to an extremely high metabolic clearance rate. When incubated at very high concentrations or in combination with a catechol O-methyltransferase (COMT) inhibitor to prevent its metabolism, 2-hydroxyestrone shows antiestrogenic effects in estrogen receptor-positive human breast cancer cells.


2-Hydroxyestrone
2-Hydroxyestrone dissociates from the estrogen receptors much more rapidly than does estradiol.


2-Hydroxyethyl terephthalic acid
2-Hydroxyethyl terephthalic acid is an organic compound with the formula HOC2H4O2CC6H4CO2H. It is the monoester of terephthalic acid and ethylene glycol. The compound is a precursor to poly(ethylene terephthalate) (PET), a polymer that is produced on a large scale industrially. 2-Hydroxyethyl terephthalic acid is a colorless solid that is soluble in water and polar organic solvents. Near neutral pH, 2-hydroxyethyl terephthalic acid converts to 2-hydroxyethyl terephthalate, HOC2H4O2CC6H4CO2−.


2-Hydroxyethyl terephthalic acid, Occurrence and reactions
2-Hydroxyethyl terephthalic acid is an intermediate in both the formation and hydrolysis of PET. It is produced on a massive scale as the first intermediate in certain routes to PET. Specifically, it is produced in the course of the thermal condensation of terephthalic acid and ethylene glycol:


2-Hydroxyethyl terephthalic acid, Occurrence and reactions
It is also produced by the partial hydrolysis of PET, as catalyzed by the enzyme PETase:


2-Hydroxyglutaric aciduria
2-hydroxyglutaric aciduria is a rare neurometabolic disorder characterized by the significantly elevated levels of hydroxyglutaric acid in one's urine. It is either autosomal recessive or autosomal dominant.


2-Hydroxyglutaric aciduria, Presentation
The signs/symptoms of this condition are consistent with the following:


2-Hydroxyglutaric aciduria, Diagnosis, Classification
2-hydroxyglutaric aciduria is an organic aciduria, and because of the stereoisomeric property of 2-hydroxyglutarate different variants of this disorder are distinguished:


2-Hydroxyglutaric aciduria, Diagnosis, Classification, L-2-hydroxyglutaric aciduria
The L-2 form is more common, severe, and mainly affects the central nervous system. The basal ganglia are affected, and cystic cavitations in the white matter of the brain are common, beginning in infancy. This form is chronic, with early symptoms such as hypotonia, tremors, and epilepsy declining into spongiform leukoencephalopathy, muscular choreodystonia, mental retardation, and psychomotor regression.


2-Hydroxyglutaric aciduria, Diagnosis, Classification, L-2-hydroxyglutaric aciduria
It is associated with L2HGDH, which encodes L-2-hydroxyglutarate dehydrogenase. L-2 -hydroxyglutarate is produced by promiscuous action of malate dehydrogenase on 2-oxoglutarate, and L-2-hydroxyglutarate dehydrogenase is an example of a metabolite repair enzyme that oxidizes L-2-hydroxyglutarate back to 2-oxoglutarate.


2-Hydroxyglutaric aciduria, Diagnosis, Classification, D-2-hydroxyglutaric aciduria
The D2 form is rare, with symptoms including macrocephaly, cardiomyopathy, mental retardation, hypotonia, and cortical blindness. It is caused by recessive mutations in D2HGDH (type I) or by dominant gain-of-function mutations in IDH2 (type II).


2-Hydroxyglutaric aciduria, Diagnosis, Classification, Combined D-2- and L-2-hydroxyglutaric aciduria
The combined form is characterized by severe early-onset epileptic encephalopathy and absence of developmental progress. It is caused by recessive mutations in SLC25A1 encoding the mitochondrial citrate carrier.


2-Hydroxyglutaric aciduria, Treatment
The treatment of 2-Hydroxyglutaric aciduria is based on seizure control, the prognosis depends on how severe the condition is.


2-Hydroxyisocaproic acid
2-Hydroxyisocaproic acid (HICA or leucic acid) is a metabolite of the branched-chain amino acid leucine. It is commonly sold as a purported muscle building supplement. It also has fungicidal properties. HICA was shown to increase protein synthesis and muscle mass in rats who were recovering from a period of induced atrophy.


2-Hydroxyisocaproic acid
HICA is also produced by several protozoans it has been reported to show anti- inflammatory activities.


2-Hydroxymuconate semialdehyde
2-Hydroxymuconate semialdehyde is formed from catechol by the enzyme catechol 2,3-dioxygenase during the degradation of benzoates. It is hydrolysed into formate and 2-oxopent-4-enoate by 2-hydroxymuconate-semialdehyde hydrolase.


2-Hydroxymuconate-6-semialdehyde dehydrogenase
2-Hydroxymuconate-6-semialdehyde dehydrogenase (EC , xylG [gene], praB [gene] ) is an enzyme with systematic name (2E,4Z)-2-hydroxy-6-oxohexa-2,4-dienoate:NAD+ oxidoreductase. This enzyme catalyses the following chemical reaction


2-Hydroxymuconate-6-semialdehyde dehydrogenase
This substrate for this enzyme is formed by meta ring cleavage of catechol (EC 1.13.11.2, catechol 2,3-dioxygenase), and is an intermediate in the bacterial degradation of several aromatic compounds.


2-Imidazolidinethione
2-Imidazolidinethione is the organosulfur compound with the formula C2H2(NH)2C=S. It is a cyclic unsaturated thiourea with a short C=S bond length of 169 pm. The compound is often referred to as 2-mercaptoimidazole, which is a tautomer that is not observed. The compound forms a variety of metal complexes. In terms of bonding and reactivity, 2-imidazolidinethione is similar to mercaptobenzimidazole.


2-Imidazoline
2-Imidazoline (Preferred IUPAC name: 4,5-dihydro-1H-imidazole) is one of three isomers of the nitrogen-containing heterocycle imidazoline, with the formula C3H6N2. The 2-imidazolines are the most common imidazolines commercially, as the ring exists in some natural products and some pharmaceuticals. They also have been examined in the context of organic synthesis, coordination chemistry, and homogeneous catalysis.


2-Imidazoline, Synthesis
A variety of routes exist for the synthesis of imidazolines, with the most common methods involving the condensation of 1,2-diamines (e.g. ethylenediamine) with nitriles or esters. The nitrile based route is essentially a cyclic Pinner reaction; it requires high temperatures and acid catalysis and is effective for both alkyl and aryl nitriles.


2-Imidazoline, Biological role
Many imidazolines are biologically active. Most bio-active derivatives bear a substituent (aryl or alkyl group) on the carbon between the nitrogen centers. Some generic names include oxymetazoline, xylometazoline, tetrahydrozoline, and naphazoline.


2-Imidazoline, Biological role, Imidazoline in Natural Products
Imidazoline has been found in various natural products. Natural molecules topsentin D and spongotine B were discovered in several marine sponges. These metabolites have received considerable attention because of their potent properties such as antitumor, antiviral, and anti-inflammatory activities.


2-Imidazoline, Biological role, Pharmaceutical Applications
2-imidazolines have been investigated as antihyperglycemic, anti-inflammatory, antihypertensive, antihypercholesterolemic, and antidepressant reagents. The imidazoline-containing drug clonidine is used alone or in combination with other medications to treat high blood pressure. It is also used in the treatment of dysmenorrhea, hypertensive crisis, Tourette's syndrome and attention deficit hyperactivity disorder (ADHD).


2-Imidazoline, Applications, Homogeneous Catalysis
As a structural analogue of 2-oxazolines, 2-imidazolines have been developed as ligands in coordination chemistry. The substitutions on the nitrogen atom in the imidazoline ring provide opportunities for fine-tuning the electronic and steric properties. Some of the complexes function as catalysts for Suzuki–Miyaura couplings, Mizoroki–Heck reactions, Diels–Alder reactions, asymmetric allylic substitution, [3,3] sigmatropic rearrangement, Henry reactions, etc.


2-Imidazoline, Applications, Surfactants
Surfactants based around 2-imidazoline, such as sodium lauroamphoacetate, are used in personal care products were mildness and non-irritancy are particularly important (e.g. baby products, "no more tears" shampoos etc. ).


2-Iminothiolane
2-Iminothiolane is a cyclic thioimidate compound also known as Traut's reagent. It is a thiolating reagent that reacts with primary amine groups, such as those of amino acids, to form sulfhydryl groups.


2-Iminothiolane, Application
2-Iminothiolane reacts with primary amines efficiently at pH 7 to 9, creating amidine compounds with a sulfhydryl group. Thus it allows for crosslinking or labeling of molecules such as proteins through use of disulfide or thioether conjugation. It was first used to thiolate a subunit of ribosome in E. coli in 1973 by Robert Traut, its namesake, and his colleagues.


2-Iminothiolane, Application
It also reacts with aliphatic and phenolic hydroxyl groups at high pH, albeit at a much slower rate.


2-Iodobenzoic acid
2-Iodobenzoic acid,  or o-iodobenzoic acid, is an organic compound with the formula IC6H4COOH. The synthesis of 2-iodobenzoic acid via the diazotization of anthranilic acid is commonly performed in university organic chemistry labs. One of its most common uses is as a precursor for the preparation of IBX and Dess–Martin periodinane, both used as mild oxidants.


2-Iodobenzoic acid, Synthesis
2-Iodobenzoic acid can be synthesized via a Sandmeyer reaction consisting of the diazotization of anthranilic acid followed by a diazo replacement. First anthranilic acid is treated with nitrous acid in order to convert the amino group into the diazo group. The diazo group is ejected, yielding a carbocation which is then attacked by highly nucleophilic I− anion.


2-Iodobenzoic acid, Synthesis
The nitrous acid is usually generated in situ from sodium nitrite.


2-Iodomelatonin
2-Iodomelatonin is a melatonin analog used as a radiolabelled ligand for the melatonin receptors, MT1, MT2, and MT3. It acts as a full agonist at both MT1 and MT2 receptors.


2-Iodoxybenzoic acid
2-Iodoxybenzoic acid (IBX) is an organic compound used in organic synthesis as an oxidizing agent. This periodinane is especially suited to oxidize alcohols to aldehydes. IBX is prepared from 2-iodobenzoic acid, potassium bromate, and sulfuric acid. Frigerio and co-workers have also demonstrated, in 1999 that potassium bromate may be replaced by commercially available Oxone. One of the main drawbacks of IBX is its limited solubility; IBX is insoluble in many common organic solvents. In the past, it was believed that IBX was shock sensitive, but it was later proposed that samples of IBX were shock sensitive due to the residual potassium bromate left from its preparation. Commercial IBX is stabilized by carboxylic acids such as benzoic acid and isophthalic acid.


2-Iodoxybenzoic acid, Reaction mechanism
The reaction mechanism for an oxidation of an alcohol to an aldehyde according to the hypervalent twisting mechanism involves a ligand exchange reaction replacing the hydroxyl group by the alcohol followed by a twist and an elimination reaction. The twist is a requirement because the iodine to oxygen double bond is oriented out of plane with the alkoxy group and the concerted elimination would not be able to take place.


2-Iodoxybenzoic acid, Reaction mechanism
This twist reaction is a rearrangement in which the oxygen atom is moved into a proper plane for a 5 membered cyclic transition state in the elimination reaction and is calculated by Computational chemistry to be the rate-determining step in the oxidation. The twist mechanism also explains why oxidation is faster for larger alcohols than for small alcohols. The twist is driven forward by the steric hindrance that exists between the ortho hydrogen atom and the protons from the alkoxy group and larger alkoxy groups create larger steric repulsion. The same computation predicts a much faster reacting IBX derivative with a 100 fold reaction rate when this ortho hydrogen atom is replaced by a methyl group thus facilitating the twist until the elimination reaction takes prevalence as the rate determining step.


2-Iodoxybenzoic acid, Reaction mechanism
IBX exists as two tautomers one of which is the carboxylic acid. The acidity of IBX which has been determined in water (pKa 2.4) and DMSO (pKa 6.65) is known to affect organic reactions, for instance acid-catalyzed isomerization accompanying oxidations.


2-Iodoxybenzoic acid, Scope
IBX is also available as silica gel or polystyrene bound IBX. In many applications, IBX is replaced by Dess–Martin periodinane which is more soluble in common organic solvents. A sample reaction is an IBX oxidation used in the total synthesis of eicosanoid:  More and Finney and Van Arman have demonstrated that common organic solvents are suitable for many IBX oxidations, despite its low solubility, and in fact may simplify product purification.


2-Iodoxybenzoic acid, Scope
In 2001, K. C. Nicolaou and co-workers published a series of papers in the Journal of the American Chemical Society demonstrating, among other transformations, the use of IBX to oxidize primary and secondary benzylic carbons to aromatic aldehydes and ketones, respectively.


2-Iodoxybenzoic acid, Scope, Oxidative cleavage
IBX is notable for oxidizing vicinal diols (or glycols) to diketones without cleavage of the carbon-carbon bond, but oxidative cleavage of glycols to two aldehydes or ketones can occur when modified conditions are used (elevated temperatures or trifluoroacetic acid solvent).


2-Iodoxybenzoic acid, Scope, Oxidative cleavage
The reaction mechanism for this glycol cleavage is based on initial formation of an adduct between 10-I-4 IBX and DMSO to a 12-I-5 intermediate 3 in which DMSO acts as a leaving group for incoming alcohol 4 to intermediate 5. One equivalent of water is split off forming 12-I-5 spirobicyclic periodinane 6 setting the stage for fragmentation to 7. With hydroxyl alpha protons present, oxidation to the acyloin competes. Trifluoroacetic acid is found to facilitate the overall reaction.


2-Iodoxybenzoic acid, Scope, α-Hydroxylations
Kirsch and co-workers were able to hydroxylate keto compounds with IBX in α-position under mild conditions. This method could be extended to β-keto esters.


2-Iodoxybenzoic acid, Scope, Oxidation of β-hydroxyketones to β-diketones
Bartlett and Beaudry discovered that IBX is a valuable reagent for the transformation of β-hydroxyketones to β-diketones. IBX provides yields superior to both the Swern and Dess–Martin oxidation protocols.


2-Ketoarginine methyltransferase
2-Ketoarginine methyltransferase (EC , mrsA (gene)) is an enzyme with systematic name S-adenosyl-L-methionine:5-carbamimidamido-2-oxopentanoate S-methyltransferase. This enzyme catalyses the following chemical reaction


2-Ketoarginine methyltransferase
The enzyme is involved in production of the rare amino acid 3-methylarginine.


2-MDP
2-MDP (U-23807A) is a dissociative anaesthetic drug which has been found to be an NMDA antagonist and produces similar effects to PCP in animals. The levo or (-) isomer is the active form of the drug. It also has stimulant effects, having only around one third the potency of amphetamine by weight, but with a long duration of action, lasting more than 24 hours from a single oral dose.


2-Me-DET
2-Me-DET, or 2-methyl-diethyltryptamine, is a lesser-known psychedelic drug. It is the 2-methyl analog of DET. 2-Me-DET was first synthesized by Alexander Shulgin. In his book TiHKAL (Tryptamines I Have Known and Loved), the minimum dosage is listed as 80-120 mg, and the duration listed as 6–8 hours. 2-Me-DET produces pitch distortion, like that of DiPT. Very little data exists about the pharmacological properties, metabolism, and toxicity of 2-Me-DET.


2-Mercaptoethanol
2-Mercaptoethanol (also β-mercaptoethanol, BME, 2BME, 2-ME or β-met) is the chemical compound with the formula HOCH2CH2SH. ME or βME, as it is commonly abbreviated, is used to reduce disulfide bonds and can act as a biological antioxidant by scavenging hydroxyl radicals (amongst others). It is widely used because the hydroxyl group confers solubility in water and lowers the volatility. Due to its diminished vapor pressure, its odor, while unpleasant, is less objectionable than related thiols.


2-Mercaptoethanol, Production
2-Mercaptoethanol is manufactured industrially by the reaction of ethylene oxide with hydrogen sulfide. Thiodiglycol and various zeolites catalyze the reaction.


2-Mercaptoethanol, Reactions
2-Mercaptoethanol reacts with aldehydes and ketones to give the corresponding oxathiolanes. This makes 2-mercaptoethanol useful as  a protecting group, giving a derivative whose stability is between that of a dioxolane and a dithiolane.


2-Mercaptoethanol, Applications, Reducing proteins
Some proteins can be denatured by 2-mercaptoethanol, which cleaves the disulfide bonds that may form between thiol groups of cysteine residues. In the case of excess 2-mercaptoethanol, the following equilibrium is shifted to the right:


2-Mercaptoethanol, Applications, Reducing proteins
By breaking the S-S bonds, both the tertiary structure and the quaternary structure of some proteins can be disrupted. Because of its ability to disrupt the structure of proteins, it was used in the analysis of proteins, for instance, to ensure that a protein solution contains monomeric protein molecules, instead of disulfide linked dimers or higher order oligomers. However, since 2-mercaptoethanol forms adducts with free cysteines and is somewhat more toxic, dithiothreitol (DTT) is generally more used especially in SDS-PAGE. DTT is also a more powerful reducing agent with a redox potential (at pH 7) of −0.33 V, compared to −0.26 V for 2-mercaptoethanol.


2-Mercaptoethanol, Applications, Reducing proteins
2-Mercaptoethanol is often used interchangeably with dithiothreitol (DTT) or the odorless tris(2-carboxyethyl)phosphine (TCEP) in biological applications.


2-Mercaptoethanol, Applications, Reducing proteins
Although 2-mercaptoethanol has a higher volatility than DTT, it is more stable: 2-mercaptoethanol's half-life is more than 100 hours at pH 6.5 and 4 hours at pH 8.5; DTT's half-life is 40 hours at pH 6.5 and 1.5 hours at pH 8.5.


2-Mercaptoethanol, Applications, Preventing protein oxidation
2-Mercaptoethanol and related reducing agents (e.g., DTT) are often included in enzymatic reactions to inhibit the oxidation of free sulfhydryl residues, and hence maintain protein activity. It is often used in enzyme assays as a standard buffer component.


2-Mercaptoethanol, Applications, Denaturing ribonucleases
2-Mercaptoethanol is used in some RNA isolation procedures to eliminate ribonuclease released during cell lysis. Numerous disulfide bonds make ribonucleases very stable enzymes, so 2-mercaptoethanol is used to reduce these disulfide bonds and irreversibly denature the proteins. This prevents them from digesting the RNA during its extraction procedure.


2-Mercaptoethanol, Safety
2-Mercaptoethanol is considered toxic, causing irritation to the nasal passageways and respiratory tract upon inhalation, irritation to the skin, vomiting and stomach pain through ingestion, and potentially death if severe exposure occurs.


2-Mercaptoindole
2-Mercaptoindole is a bicyclic heterocycle containing a thiol group. It is a popular ligand and building block for more complex structures.


2-Mercaptopyridine
2-Mercaptopyridine is an organosulfur compound with the formula HSC5H4N. This yellow crystalline solid is a derivative of pyridine. The compound and its derivatives serve primarily as acylating agents. A few of 2-mercaptopyridine’s other uses include serving as a protecting group for amines and imides as well as forming a selective reducing agent. 2-Mercaptopyridine oxidizes to 2,2’-dipyridyl disulfide.


2-Mercaptopyridine, Preparation
2-Mercaptopyridine was originally synthesized in 1931 by heating 2-chloropyridine with calcium hydrogen sulfide.


2-Mercaptopyridine, Preparation
A more convenient route to 2-mercaptopyridine is the reaction of 2-chloropyridine and thiourea in ethanol and aqueous ammonia.


2-Mercaptopyridine, Preparation
2-Mercaptopyridine derivatives can also be generated from precursors lacking preformed pyridine rings. It arises for example in the condensation of α,β-unsaturated ketones, malononitrile, and 4-methylbenzenethiol under microwave irradiation. The reaction is conducted with a base catalyst.


2-Mercaptopyridine, Structure and properties
Similar in nature to 2-hydroxypyridine, 2-mercaptopyridine converts to the thione (or more accurately thioamide) tautomer. The preferred form is dependent on temperature, concentration, and solvent. The thione is favored at lower temperatures, lower concentrations, and in less polar solvents. 2-Mercaptopyridine is favored in dilute solutions and in solvents capable of hydrogen bonding. These solvents will compete with other 2-mercaptopyridines to prevent self association.


2-Mercaptopyridine, Structure and properties
The association constant for this reaction between mutual 2-mercaptopyridines is described below. The ratio is of monosulfide to disulfide in chloroform.


2-Mercaptopyridine, Reactions
2-Mercaptopyridine oxidizes to 2,2’-dipyridyl disulfide. As amines are good catalysts for the oxidation of thiols to disulfides, this process is autocatalytic.


2-Mercaptopyridine, Reactions
2-Mercaptopyridine can also be prepared by hydride reduction of 2,2’-dipyridyl disulfide.


2-Mercaptopyridine, Main reactions
2-Mercaptopyridine and the disulfide are chelating ligands. 2-mercaptopyridine forms the indium(III) complex In(PyS)3 complexes in supercritical carbon dioxide. 2-Mercaptopyridine may also be used to coat porous media in order to purify plasmid DNA of impurities such as RNA and proteins at relatively quick timescales to similar methods. 2-Mercaptopyridine is also used acylate phenols, amines, and carboxylic acids.


2-Mercaptopyridine, Main reactions
Another application lies in metal-free catalysis: 2-mercaptopyridine can be used as a catalyst for isodesmic C-H borylation of heteroarenes. The particular pattern of Lewis base and Brønsted acid allows to cleave boron-carbons bonds and then form a new boron-carbon bond by lewis pair mediated C-H activation.


2-Methoxy-4-vinylphenol
2-Methoxy-4-vinylphenol is an aromatic substance used as a flavoring agent. It is one of the compounds responsible for the natural aroma of buckwheat.


2-Methoxy-4-vinylphenol
Some insects such as Rhynchophorus ferrugineus (Red palm weevil) use this substance for chemical signaling (pheromones).


2-Methoxy-4-vinylphenol
The aroma of pure substance was described as: apple, spicy, peanut, wine-like or clove and curry.


2-Methoxy-4-vinylphenol
Ferulic acid is converted by certain strains of yeast, notably strains used in brewing of wheat beers, such as Torulaspora delbrueckii to 2-methoxy-4-vinylphenol which gives beers such as Weissbier and Wit their distinctive "clove" flavor. Saccharomyces cerevisiae (brewer's yeast) and Pseudomonas fluorescens are also able to convert trans-ferulic acid into 2-methoxy-4-vinylphenol.


2-Methoxy-6-polyprenyl-1,4-benzoquinol methylase
2-Methoxy-6-polyprenyl-1,4-benzoquinol methylase (EC , ubiE (gene)) is an enzyme with systematic name S-adenosyl-L-methionine:2-methoxy-6-all-trans-polyprenyl-1,4-benzoquinol 5-C-methyltransferase. This enzyme catalyses the following chemical reaction


2-Methoxyamphetamine
2-Methoxyamphetamine (2-MA), also known as ortho-methoxyamphetamine (OMA), is a drug of the amphetamine class. It is substantially weaker in inhibiting the reuptake of and inducing the release of the monoamine neurotransmitters compared to related agents such as amphetamine, MMA, and PMA, and may instead act as a β-adrenergic receptor agonist similarly to its N-methylated analogue methoxyphenamine.


2-Methoxybenzaldehyde
2-Methoxybenzaldehyde is an organic compound with the formula CH3OC6H4CHO. The molecule consists of a benzene ring with formyl and a methoxy groups on adjacent positions. It is a colorless solid with a pleasant aroma. The related isomer 4-anisaldehyde is a better known, being a commercial flavorant. 2 -Anisaldehyde is prepared commercially by formylation of anisole.


2-Methoxyestradiol
2-Methoxyestradiol (2-ME2, 2-MeO-E2) is a natural metabolite of estradiol and 2-hydroxyestradiol (2-OHE2). It is specifically the 2-methyl ether of 2-hydroxyestradiol. 2 -Methoxyestradiol prevents the formation of new blood vessels that tumors need in order to grow (angiogenesis), hence it is an angiogenesis inhibitor. It also acts as a vasodilator and induces apoptosis in some cancer cell lines. 2-Methoxyestradiol is derived from estradiol, although it interacts poorly with the estrogen receptors (2,000-fold lower activational potency relative to estradiol). However, it retains activity as a high-affinity agonist of the G protein-coupled estrogen receptor (GPER) (10 nM, relative to 3–6 nM for estradiol).


2-Methoxyestradiol, Clinical development
2-Methoxyestradiol was being developed as an experimental drug candidate with the tentative brand name Panzem. It has undergone Phase 1 clinical trials against breast cancer. A phase II trial of 18 advanced ovarian cancer patients reported encouraging results in October 2007.


2-Methoxyestradiol, Clinical development
Preclinical models also suggest that 2-methoxyestradiol could also be effective against inflammatory diseases such as rheumatoid arthritis. Several studies have been conducted showing 2-methoxyestradiol is a microtubule inhibitor and is inhibitory against prostate cancer in rodents.


2-Methoxyestradiol, Clinical development
As of 2015, all clinical development of 2-methoxyestradiol has been suspended or discontinued. This is significantly due to the very poor oral bioavailability of the molecule and also due to its extensive metabolism. Analogues have been developed in an attempt to overcome these problems. An example is 2-methoxyestradiol disulfamate (STX-140), the C3 and C17β disulfamate ester of 2-methoxyestradiol.


2-Methoxyestradiol, Clinical effects
2-Methoxyestradiol was found to increase sex hormone-binding globulin (SHBG) levels in men by 2.5-fold at a dose of 400 mg/day and by 4-fold at a dose of 1,200 mg/day. Conversely, it did not seem to suppress testosterone levels.


2-Methoxyestradiol disulfamate
2-Methoxyestradiol disulfamate (developmental code STX-140; also known as 2-methoxyestradiol 3,17β-O,O-bis(sulfamate)) is a synthetic, oral active anti-cancer medication which was previously under development for potential clinical use. It has improved potency, low metabolism, and good pharmacokinetic properties relative to 2-methoxyestradiol (2-MeO-E2). It is also a potent inhibitor of steroid sulfatase, the enzyme that catalyzes the desulfation of steroids such as estrone sulfate and dehydroepiandrosterone sulfate (DHEA-S).


2-Methoxyestradiol disulfamate
2-Methoxyestradiol disulfamate exhibits anti-angiogenic activity and induction of cell cycle arrest and apoptosis in human tumor xenografts, with clinical potential for hormone–independent tumors. Some of this activity stems from tubulin binding at the colchicine site and disruption of interphase microtubules. 2 -Methoxyestradiol disulfamate is highly active in tumors that are resistant to chemotherapy.


2-Methoxyestradiol disulfamate
In xenograft models of breast and prostate cancer complete cures were achieved after oral treatment with 2-methoxyestradiol disulfamate and drug-resistant tumors also shrank in size after oral treatment. Conventional treatments for hormone-independent cancers targeting tubulin are associated with side effects, such as neurotoxicity, and can only be given infrequently and intravenously. 2 -Methoxyestradiol disulfamate is more effective on the same tumors, blocks metastatic spread without the peripheral neuropathy associated with current clinical anticancer drugs.


2-Methoxyestriol
2-Methoxyestriol (2-MeO-E3) is an endogenous estrogen metabolite. It is specifically a metabolite of estriol and 2-hydroxyestriol. It has negligible affinity for the estrogen receptors and no estrogenic activity. However, 2-methoxyestriol does have some non-estrogen receptor-mediated cholesterol-lowering effects.


2-Methoxyestrone
2-Methoxyestrone (2-ME1) is an endogenous, naturally occurring methoxylated catechol estrogen and metabolite of estrone that is formed by catechol O-methyltransferase via the intermediate 2-hydroxyestrone. Unlike estrone but similarly to 2-hydroxyestrone and 2-methoxyestradiol, 2-methoxyestrone has very low affinity for the estrogen receptor and lacks significant estrogenic activity.


2-Methoxyethanol
2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C3H8O2 that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer:


2-Methoxyethanol
2-Methoxyethanol is used as a solvent for many different purposes such as varnishes, dyes, and resins. It is also used as an additive in airplane deicing solutions. In organometallic chemistry it is commonly used for the synthesis of Vaska's complex and related compounds such as carbonylchlorohydridotris(triphenylphosphine)ruthenium (II). During these reactions the alcohol acts as a source of hydride and carbon monoxide.


2-Methoxyethanol
2-Methoxyethanol is toxic to the bone marrow and testicles. Workers exposed to high levels are at risk for granulocytopenia, macrocytic anemia, oligospermia, and azoospermia.


2-Methoxyethanol
The methoxyethanol is converted by alcohol dehydrogenase into methoxyacetic acid which is the substance which causes the harmful effects. Both ethanol and acetate have a protecting effect. The methoxyacetate can enter the Krebs cycle where it forms methoxycitrate.


2-Methoxyethyl-18-methoxycoronaridinate
(–)-2-Methoxyethyl-18-methoxycoronaridinate (ME-18-MC) is a second generation synthetic derivative of ibogaine developed by the research team led by the pharmacologist Stanley D. Glick from the Albany Medical College and the chemist Martin E. Kuehne from the University of Vermont. In animal studies it has shown similar efficacy to the related compound 18-methoxycoronaridine (18-MC) at reducing self-administration of morphine and methamphetamine but with higher potency by weight, showing anti-addictive effects at the equivalent of half the minimum effective dose of 18-MC.


2-Methoxyethyl-18-methoxycoronaridinate
Similarly to 18-MC itself, ME-18-MC acts primarily as a selective α3β4 nicotinic acetylcholine antagonist, although it has a slightly stronger effect than 18-MC as an NMDA antagonist, and its effects on opioid receptors are weaker than those of 18-MC at all except the kappa opioid receptor, at which it has slightly higher affinity than 18-MC.


2-Methoxypropene
2-Methoxypropene is an ether with the chemical formula C4H8O. It is a reagent used in organic synthesis as a protecting group for alcohols, and the conversion diols to the acetonide group.


2-Methoxypropene
2-Methoxypropene can be prepared by the elimination of methanol from dimethoxypropane, or by the addition of methanol to propyne or allene.


2-Methyl-1-butanol
2-Methyl-1-butanol (IUPAC name, also called active amyl alcohol) is an organic compound with the formula CH3CH2CH(CH3)CH2OH. It is one of several isomers of amyl alcohol. A colorless liquid, it occurs naturally in trace amounts and has attracted some attention as a potential biofuel, exploiting its hydrophobic (gasoline-like) and branched structure. It is chiral.


2-Methyl-1-butanol, Occurrence
2-Methyl-1-butanol is a component of many mixtures of commercial amyl alcohols. It is one of the many components of the aroma of various fungi and fruit, e.g., the summer truffle, tomato, and cantaloupe.


2-Methyl-1-butanol, Production and reactions
2-Methyl-1-butanol has been produced from glucose by genetically modified E. coli. 2-Keto-3-methylvalerate, a precursor to threonine, is converted to the target alcohol by the sequential action of 2-keto acid decarboxylase and dehydrogenase. It can be derived from fusel oil (because it occurs naturally in fruits such as grapes) or manufactured by either the oxo process or via the halogenation of pentane.


2-Methyl-1-pentanol
2-Methyl-1-pentanol (IUPAC name: 2-methylpentan-1-ol) is an organic chemical compound. It is used as a solvent and an intermediate in the manufacture of other chemicals.


2-Methyl-2,4-pentanediol
2-Methyl-2,4-pentanediol (MPD) is an organic compound with the formula (CH3)2C(OH)CH2CH(OH)CH3. This colourless liquid is a chiral diol. It is produced industrially from diacetone alcohol by hydrogenation. Total European and USA production was 15000 tonnes in 2000.


2-Methyl-2,4-pentanediol
2-Methyl-2,4-pentanediol exists as two enantiomers, (4R)-(-) and (4S)-(+). In the Protein Data Bank, the 3-letter code "MPD" refers to the (S)-(-) enantiomer, while "MRD" is used to refer to the (R)-(+) version. Commercial products labeled "MPD" are usually the racemate, also sold as and referred to as "hexylene glycol".


2-Methyl-2,4-pentanediol, Uses
2-Methyl-2,4-pentanediol exhibits both surfactant and emulsion-stabilizing properties. Its relatively high viscosity and low volatility are advantageous in coatings, cleansers, cosmetics, solvents, and hydraulic fluids. Although it is an irritant at higher concentrations, it is sometimes used in skin care, hair care, soap, and eye cosmetic products at concentrations ranging from 0.1% - 25%.


2-Methyl-2,4-pentanediol, Uses
It is biodegradable and unlikely to accumulate in the environment.


2-Methyl-2,4-pentanediol, Laboratory uses
In the laboratory it is a common precipitant and cryoprotectant in protein crystallography. Since hexylene glycol is compatible with polar and nonpolar molecules, it competes with the solvent in a crystallography experiment causing the protein to precipitate. Hexylene glycol is so effective in protein crystallography because its amphiphilic nature and small, flexible structure allows it to bind to many different locations on a protein secondary structure including alpha helices and beta sheets. When hexylene glycol binds to these different locations, water is removed and the protein crystals anneal, which prevents ice formation during cryocrystallography techniques. Incorporation of hexylene glycol into solution has been known to improve the resolution of X-ray diffraction making protein structures easily identifiable. Additionally hexylene glycol is not a strong denaturing agent and thus does not significantly alter the structure of a protein during the crystallography procedure.


2-Methyl-2-butene
2-Methyl-2-butene, 2m2b, 2-methylbut-2-ene, also amylene is an alkene hydrocarbon with the molecular formula C5H10.


2-Methyl-2-butene
Used as a free radical scavenger in trichloromethane (chloroform) and dichloromethane (methylene chloride).


2-Methyl-2-butene
John Snow, the English physician,  experimented with it in the 1840s as an anesthetic, but stopped using it for unknown reasons.


2-Methyl-2-heptanethiol
2-Methyl-2-heptanethiol is an organic compound classified as a thiol. It is a straw-colored liquid with a strong, obnoxious odor.


2-Methyl-2-heptanethiol
It is used as a lubricant additive and in polymer modification. The chemical is one of the tertiary aliphatic mercaptans (thiols) synthesized from petroleum, as described in a 1950 paper. Initial research postulated they could be used as lubricant additives, ore flotation collectors, vulcanization accelerators, fungicides, and nonionic detergents.


2-Methyl-2-nitrosopropane
2-Methyl-2-nitrosopropane (MNP or t-nitrosobutane) is the organic compound with the formula (CH3)3CNO. It is a blue liquid that is used in chemical research as a spin trap, i.e. it binds to radicals.


2-Methyl-2-nitrosopropane, Preparation and structure
The freshly distilled compound is a blue volatile liquid. Like other nitroso compounds, it features a bent C-N=O linkage. Upon standing at room temperature, the blue liquid converts to the colourless solid that is the dimer (m.p. 74-75 °C). In solution, this dimer quickly reverts to the blue monomer.


2-Methyl-2-nitrosopropane, Reactions
It can be used as a spin trap. This molecule traps unstable free radicals to form stable paramagnetic nitroxide radicals that can be detected and analyzed by electron spin resonance spectroscopy. It is particularly useful for trapping carbon-centered tyrosyl radicals. It has also been used in organic chemistry as electrophile to transform sulfones into aldehydes.


2-Methyl-2-nitrosopropane, Reactions
MNP is also an efficient regulator of the radical polymerization of methyl methacrylate through the 'pseudoliving' chain mechanism.


2-Methyl-2-pentanol
2-Methyl-2-pentanol (IUPAC name: 2-methylpentan-2-ol) is an organic chemical compound. It can be added to a gas chromatograph to help distinguish between branched compounds, especially alcohols. Its presence in urine can be used to test for exposure to 2-methylpentane. As with many other short-chain alcohols, 2-methyl-2-pentanol can produce intoxication and sedative effects similar to those of ethanol, though it is more irritating to mucous membranes and generally more toxic to the body.


2-Methyl-2-propyl-1,3-propanediol
2-Methyl-2-propyl-1,3-propanediol (MPP) is a simple alkyl diol which has sedative, anticonvulsant and muscle relaxant effects. It is both a synthetic precursor to, and an active metabolite of the tranquilizers meprobamate and carisoprodol, as well as other derivatives.


2-Methyl-3-oxopropanoic acid
2-Methyl-3-oxopropanoic acid (or methylmalonate semialdehyde) is an intermediate in the metabolism of valine.


2-Methyl-3-pentanol
2-Methyl-3-pentanol (IUPAC name: 2-methylpentan-3-ol) is an organic chemical compound. It is used as a fuel.


2-Methyl-5-hydroxytryptamine
2-Methyl-5-hydroxytryptamine (2-Methylserotonin, 2-Methyl-5-HT) is a tryptamine derivative closely related to the neurotransmitter serotonin which acts as a moderately selective full agonist at the 5-HT3 receptor.


2-Methyl-6-(phenylethynyl)pyridine
2 -Methyl-6-(phenylethynyl)pyridine (MPEP) is a research drug which was one of the first compounds found to act as a selective antagonist for the metabotropic glutamate receptor subtype mGluR5. After being originally patented as a liquid crystal for LCDs, it was developed by the pharmaceutical company Novartis in the late 1990s.


2-Methyl-6-(phenylethynyl)pyridine
It was found to produce neuroprotective effects following acute brain injury in animal studies, although it was unclear whether these results were purely from mGluR5 blockade as it also acts as a weak NMDA antagonist, and as a positive allosteric modulator of another subtype mGlu4, and there is also evidence for a functional interaction between mGluR5 and NMDA receptors in the same populations of neurons. It was also shown to produce antidepressant and anxiolytic effects in animals, and to reduce the effects of morphine withdrawal, most likely due to direct interaction between mGluR5 and the μ-opioid receptor.


2-Methyl-6-(phenylethynyl)pyridine
The main significance of MPEP has been as a lead compound to develop more potent and selective mGluR5 antagonists such as MTEP, but research using MPEP itself continues, and recently it was shown to reduce self-administration of nicotine, cocaine, ketamine and heroin in animals, possibly through an MPEP-induced potentiation of the rewarding effect of the self-administered drug, and MPEP was also shown to possess weak reinforcing effects by itself.


2-Methyl-6-nitrobenzoic anhydride
2-Methyl-6-nitrobenzoic anhydride is an organic acid anhydride also known as the Shiina reagent, having a structure wherein carboxylic acids undergo intermolecular dehydration condensation. It was developed in 2002 by Prof. Isamu Shiina (Tokyo University of Science, Japan). The compound is often abbreviated MNBA.


2-Methyl-6-nitrobenzoic anhydride, Abstract
The reagent is used for synthetic reactions wherein medium- and large-sized lactones are formed from hydroxycarboxylic acids via intramolecular ring closure (Shiina macrolactonization). The reaction proceeds at room temperature under basic or neutral conditions. This reagent can be used not only for macrolactonization but also for esterification, amidation, and peptide coupling.


2-Methyl-MDA
2-Methyl-3,4-methylenedioxyamphetamine (2-methyl-MDA) is an entactogen and psychedelic drug of the amphetamine class. It acts as a selective serotonin releasing agent (SSRA), with IC50 values of 93nM, 12,000nM, and 1,937nM for serotonin, dopamine, and norepinephrine efflux. 2-Methyl-MDA is more potent than MDA and 5-methyl-MDA. However, it is slightly more selective for serotonin over dopamine and norepinephrine release in comparison to 5-methyl-MDA.


2-Methylanthraquinone
2-Methylanthraquinone, an organic compound, is a methylated derivative of anthraquinone. An off-white solid, it is an important precursor to many dyes.


2-Methylanthraquinone, Synthesis and reactions
The compound is produced by the reaction of phthalic anhydride and toluene. It can be chlorinated to give 1-chloro-2-methylanthraquinone. Nitration gives 1-nitro-2-methylanthraquinone, which can be reduced to 1-amino-2-methyl derivative. Oxidation of the methyl group gives anthraquinone-2-carboxylic acid.


2-Methylbenzaldehyde
2-Methylbenzaldehyde is an organic compound with the formula CH3C6H4CHO. It is a colorless liquid.


2-Methylbenzaldehyde, Use and occurrence
Of its many reactions, 2-methylbenzaldehyde undergoes BF3-induced Rothemund condensation with pyrrole to give atropoisomers of tetrakis(o-tolyl)porphyrin.


2-Methylbenzaldehyde, Use and occurrence
It is one of main benzaldehyde component of automobile exhaust.


2-Methylbut-3-yn-2-ol
2-Methylbut-3-yn-2-ol is the organic compound with the formula HC2C(OH)Me2 (Me = CH3). A colorless liquid, it is classified as an alkynyl alcohol.


2-Methylbut-3-yn-2-ol, Preparation and use
It arises from the condensation of acetylene and acetone. The addition can be promoted with base or with Lewis acid catalysts. 2-Methylbut-3-yn-2-ol is produced on an industrial scale as a precursor to terpenes and terpenoids.


2-Methylbut-3-yn-2-ol, Preparation and use
2-Methylbut-3-yn-2-ol also is used as a monoprotected version of acetylene. For example, after arylation at carbon, the acetone can be removed with base:


2-Methylbutanoic acid
2-Methylbutanoic acid, also known as 2-methylbutyric acid is a branched-chain alkyl carboxylic acid with the chemical formula CH3CH2CH(CH3)CO2H, classified as a short-chain fatty acid. It exists in two enantiomeric forms, (R)- and (S)-2-methylbutanoic acid. (R)-2-methylbutanoic acid occurs naturally in cocoa beans and (S)-2-methylbutanoic occurs in many fruits such as apples and apricots, as well as in the scent of the orchid Luisia curtisii.


2-Methylbutanoic acid, History
2-Methylbutanoic acid is a minor constituent of Angelica archangelica and the perennial flowering plant valerian (Valeriana officinalis), where it co-occurs with valeric acid and isovaleric acid. The dried root of this plant has been used medicinally since antiquity. The chemical identity of all three compounds was first investigated in the 19th century by oxidation of the components of fusel alcohol, which includes the five-carbon amyl alcohols. Among the products isolated was a compound which gave a (+) rotation in polarised light, indicating it to be the (2S) isomer.


2-Methylbutanoic acid, Preparation
Racemic 2-methylbutanoic acid can readily be prepared by a Grignard reaction using 2-chlorobutane and carbon dioxide. It was the target of the first enantioselective synthesis in 1904 when the German chemist W. Marckwald heated ethyl(methyl)malonic acid with the chiral base brucine and obtained an optically active product mixture. Either enantiomer of 2-methylbutanoic acid can now be obtained by asymmetric hydrogenation of tiglic acid using a ruthenium-BINAP catalyst.