1,2-Dichloro-4-nitrobenzene
1,2-Dichloro-4-nitrobenzene is an organic compound with the formula 1,2-Cl2C6H3-4-NO2. This pale yellow solid is related to 1,2-dichlorobenzene by the replacement of one H atom with a nitro functional group. This compound is an intermediate in the synthesis of agrochemicals.


1,2-Dichloro-4-nitrobenzene, Production and uses
The nitration of  1,2-dichlorobenzene mainly produces 1,2-dichloro-4-nitrobenzene, together with smaller amounts of the 3-nitro isomer. It can also be prepared by chlorination of 1-chloro-4-nitrobenzene.


1,2-Dichloro-4-nitrobenzene, Production and uses
One of the chlorides is reactive toward nucleophiles. Potassium fluoride gives 2-chloro-1-fluoro-4-nitrobenzene, an intermediate in the production of herbicides. With ammonia, one obtains 2-chloro-4-nitroaniline, a precursor to diazo dyes. Reduction with iron powder gives 3,4-dichloroaniline (m.p. 72 °C, CAS# 95-76-1).


1,2-Dichlorobenzene
1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an organic compound with the formula C6H4Cl2. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of benzene, consisting of two adjacent chlorine atoms.


1,2-Dichlorobenzene
It is mainly used as a precursor chemical in the synthesis of agrochemicals, as a preferred solvent for dissolving and working with fullerenes, as an insecticide, and in softening and removing carbon-based contamination on metal surfaces.


1,2-Dichlorobenzene, Production and uses
1,2-Dichlorobenzene is obtained as a side-product of the production of chlorobenzene:


1,2-Dichlorobenzene, Production and uses
The reaction also affords the 1,4- and small amounts of the 1,3-isomer. The 1,4- isomer is preferred over the 1,2- isomer due to steric hindrance. The 1,3- isomer is uncommon because it is a meta- compound, while chlorine, like all halogens, is an ortho/para- director in terms of electrophilic aromatic substitution.


1,2-Dichlorobenzene, Production and uses
It is mainly used as a precursor to 1,2-dichloro-4-nitrobenzene, an intermediate in the synthesis of agrochemicals. In terms of niche applications, 1,2-dichlorobenzene is a versatile, high-boiling solvent. It is a preferred solvent for dissolving and working with fullerenes. It is an insecticide for termites and locust borers, historically used by the United States Forest Service to combat widespread bark beetle outbreaks.


1,2-Dichlorobenzene, Production and uses
1,2-Dichlorobenzene is also used in softening and removing carbon-based contamination on metal surfaces.


1,2-Dichlorobenzene, Safety
Data from human exposure to 1,2-dichlorobenzene shows that concentrations of 100 ppm have been reported to cause sporadic irritation of the eyes and respiratory tract. The Occupational Safety and Health Administration and the National Institute for Occupational Safety and Health have set occupational exposure limits at a ceiling of 50 ppm, over an eight-hour workday.


1,2-Dichloroethane
The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl chloride, which is used to make polyvinyl chloride (PVC) pipes, furniture and automobile upholstery, wall coverings, housewares, and automobile parts. 1,2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds, and as a solvent. It forms azeotropes with many other solvents, including water (at a boiling point of 70.5 °C or 158.9 °F or 343.6 K) and other chlorocarbons.


1,2-Dichloroethane, History
In 1794, physician Jan Rudolph Deiman, merchant Adriaan Paets van Troostwijk, chemist Anthoni Lauwerenburg, and botanist Nicolaas Bondt, under the name of Society of Dutch Chemists (Dutch: Gezelschap der Hollandsche Scheikundigen), were the first to produce 1,2-dichloroethane from olefiant gas (oil-making gas, ethylene) and chlorine gas. Although the Gezelschap in practice did not do much in-depth scientific research, they and their publications were highly regarded. Part of that acknowledgement is that 1,2-dichloroethane was called "Dutch oil" in old chemistry. This is also the origin of the archaic term "olefiant gas" (oil-making gas) for ethylene, for in this reaction it is ethylene that makes the Dutch oil. And "olefiant gas" is the etymological origin of the modern term "olefins", the family of hydrocarbons of which ethylene is the first member.


1,2-Dichloroethane, Production
Nearly 20 million tons of 1,2-dichloroethane are produced annually in the United States, Western Europe, and Japan. Production is primarily achieved through the iron(III) chloride-catalysed reaction of ethylene and chlorine:


1,2-Dichloroethane, Production
1,2-dichloroethane is also generated by the copper(II) chloride-catalysed oxychlorination of ethylene:


1,2-Dichloroethane, Uses, Vinyl chloride monomer (VCM) production
Approximately 95% of the world's production of 1,2-dichloroethane is used in the production of vinyl chloride monomer (VCM, chloroethene) with hydrogen chloride as a byproduct. VCM is the precursor to polyvinyl chloride.


1,2-Dichloroethane, Uses, Vinyl chloride monomer (VCM) production
The hydrogen chloride can be re-used in the production of more 1,2-dichloroethane via the oxychlorination route described above.


1,2-Dichloroethane, Uses, Other uses
1,2-Dichloroethane has been used as degreaser and paint remover but is now banned from use due to its toxicity and possible carcinogenity. As a useful 'building block' reagent, it is used as an intermediate in  the production of diverse organic compounds such as ethylenediamine. In the laboratory it is occasionally used as a source of chlorine, with elimination of ethene and chloride.


1,2-Dichloroethane, Uses, Other uses
Via several steps, 1,2-dichloroethane is a precursor to 1,1,1-trichloroethane, which is used in dry cleaning. Historically, 1,2-dichloroethane was used as an anti-knock additive in leaded fuels to scavenge lead from cylinders  and valves preventing buildup .


1,2-Dichloroethane, Safety
1,2-Dichloroethane is toxic (especially by inhalation due to its high vapour pressure), highly flammable, and possibly carcinogenic. Its high solubility and 50-year half-life in anoxic aquifers make it a perennial pollutant and health risk that is very expensive to treat conventionally, requiring a method of bioremediation. While the chemical is not used in consumer products manufactured in the U.S., a case was reported in 2009 of molded plastic consumer products (toys and holiday decorations) from China that released 1,2-dichloroethane into homes at levels high enough to produce cancer risk. Substitutes are recommended and will vary according to application. Dioxolane and toluene are possible substitutes as solvents. Dichloroethane is unstable in the presence of aluminium metal and, when moist, with zinc and iron.


1,2-Dichloroethane (data page), Vapor pressure of liquid
Table data obtained from CRC Handbook of Chemistry and Physics 44th ed. The (s) annotation indicates temperature is equilibrium of vapor over solid. Otherwise temperature is equilibrium of vapor over liquid.


1,2-Dichloroethene
1,2-Dichloroethene, commonly called 1,2-dichloroethylene or 1,2-DCE, is an organochloride with the molecular formula C2H2Cl2. It is a highly flammable, colorless liquid with a sharp, harsh odor. It can exist as either of two geometric isomers, cis-1,2-dichloroethene or trans-1,2-dichloroethene, but is often used as a mixture of the two. They have modest solubility in water. These compounds have few industrial applications, although they are fundamental given their simple stoichiometries.


1,2-Dichloroethene, Production
cis-DCE, the Z isomer,  is obtainable by the controlled chlorination of acetylene:


1,2-Dichloroethene, Production
Industrially both isomers arise as byproduct of the production of vinyl chloride, which is produced on a vast scale. Unlike vinyl chloride, the 1,2-dichloroethylene isomers do not polymerize.


1,2-Dichloroethene, Production
trans-DCE has applications including electronics cleaning, precision cleaning, and certain metal cleaning applications.


1,2-Dichloroethene, E-Z relative stability
In contrast to most cis-trans compounds, the Z isomer (cis) is more stable than the E isomer (trans) by 0.4 kcal/mol.


1,2-Dichloroethyl acetate
1,2-Dichloroethyl acetate is a chemical compound used in the making of other organic chemicals. It is a liquid which is either white or resembles water.


1,2-Dichloropropane
1,2-Dichloropropane is an organic compound classified as a chlorocarbon. It is a colorless, flammable liquid with a sweet odor. it is obtained as a byproduct of the production of epichlorohydrin, which is produced on a large scale.


1,2-Dichloropropane, Uses
1,2-Dichloropropane is an intermediate in the production of perchloroethylene and other chlorinated chemicals. It was once used as a soil fumigant, chemical intermediate,kort2137 as well as an industrial solvent and was found in paint strippers, varnishes, and furniture finish removers but some of these uses have been discontinued.


1,2-Dichloropropane, Carcinogenity
Following several cases of bile duct cancer among Japanese printing firm employees, an investigation by the Japanese Ministry of Health, Labour and Welfare concluded in March 2013 that these cases were likely due to the use of cleaning agents containing 1,2-dichloropropane. Thus, there is reasonable evidence that 1,2-dichloropropane may be a carcinogen.


1,2-Dichloropropane, Carcinogenity
Data from animal studies show tumor growth in the liver and mammary glands. Further animal studies involving inhalation toxicity data has caused the National Institute for Occupational Safety and Health to classify 1,2-dichloropropane as a carcinogen and IDLH.


1,2-Dichlorotetrafluoroethane
1,2-Dichlorotetrafluoroethane, or R-114, also known as cryofluorane (INN), is a chlorofluorocarbon (CFC) with the molecular formula ClF2CCF2Cl. Its primary use has been as a refrigerant. It is a non-flammable gas with a sweetish, chloroform-like odor with the critical point occurring at 145.6 °C and 3.26 MPa. When pressurized or cooled, it is a colorless liquid. It is listed on the Intergovernmental Panel on Climate Change's list of ozone depleting chemicals, and is classified as a Montreal Protocol Class I, group 1 ozone depleting substance.


1,2-Dichlorotetrafluoroethane
When used as a refrigerant, R-114 is classified as a medium pressure refrigerant.


1,2-Dichlorotetrafluoroethane
The U.S. Navy uses R-114 in its centrifugal chillers in preference to R-11 to avoid air and moisture leakage into the system. While the evaporator of an R-11 charged chiller runs at a vacuum during operation, R-114 yields approximately 0 psig operating pressure in the evaporator.


1,2-Difluorobenzene
1,2-Difluorobenzene, also known as DFB, is an aromatic compound with formula C6H4F2. This colorless liquid is a solvent used in the electrochemical studies of transition metal complexes.


1,2-Difluorobenzene, Synthesis
1,2-Difluorobenzene is prepared by a simple substitution reaction of fluorine with fluorobenzene.


1,2-Difluorobenzene, Synthesis
The 1,4-isomer and small amounts of the 1,3-isomer are also produced in the reaction as the fluorine group on the aromatic ring of fluorobenzene is ortho- and para- directing.


1,2-Difluorobenzene, Applications
1,2-Difluorobenzene has been used as solvent for the electrochemical analysis of transition metal complexes. It is relatively chemically inert, weakly coordinating, and has a dielectric constant high enough to dissolve many electrolytes and metal complex salts. It is used as a weakly coordinating solvent for metal complexes, alternative to the relatively more strongly coordinating solvents acetonitrile, DMSO, and DMF.


1,2-Difluorobenzene, Applications
1,2-Difluorobenzene can be acylated to 3',4'-difluoropropiophenone, which has interesting application in the synthesis of halogenated cathinone/PPA congeners.


1,2-Difluorobenzene, Hazards
DFB is a highly flammable liquid and vapour. Hazardous decomposition products formed under fire conditions include carbon oxides, and hydrogen fluoride. Handle with thick fluorinated rubber gloves.


1,2-Difluoroethane
1,2-Difluoroethane is a saturated hydrofluorocarbon containing an atom of fluorine attached to each of two carbons atoms. The formula can be written CH2FCH2F. It is an isomer of 1,1-difluoroethane. It has a HFC name of HFC-152 with no letter suffix. When cooled to cryogenic temperatures it can have different conformers, gauche and trans. In the liquid form these are about equally abundant and easily interconvert. As a gas it is mostly the gauche form.


1,2-Difluoroethane
In the HFC-152 designation, 2 means two fluorine atoms, 5 means 5-1 or four hydrogen atoms, and 1 means 1+1 or two carbon atoms.


1,2-Difluoroethane, Formation
Ethylene reacts explosively with fluorine yielding a mixture of 1,2-difluoroethane and vinyl fluoride. With solid fluorine it will react when triggered by near-infrared radiation.


1,2-Difluoroethane, Properties
If a C-H bond is over excited with too much vibration, the intramolecular vibrational relaxation takes 490 picoseconds.


1,2-Difluoroethane, Properties
The F-C-C-F dihedral angle is about 72°. Natural bond orbital deletion bond calculations show that 1,2-difluoroethane prefers the gauche conformation due to hyperconjugation effects. Since F is much more electronegative than the C atom, it will have greater electron density for the bonding orbital (Carbon-fluorine bond). Thus, C will have larger σ* orbital, which is stabilized through C-H hyperconjugation. This cis C-H bonds and the C-F σ* interactions are significant. The dihedral angle of about 72° is a result of decreasing hyper conjugative stability and decreasing steric destabilization.


1,2-Difluoroethane, Reactions
CH2FCH2F reacts with chlorine when treated with light. Two products are formed CH2FCCl2F and CHClFCHClF. The proportions of each depends on the solvent.


1,2-Difluoroethane, Uses
1,2-Difluoroethane is primarily used in Refrigerants, 39%; foam blowing agents, 17%; solvents, 14%; fluoropolymers, 14%; sterilant gas, 2%; aerosol propellants, 2%; food freezant, 1%; other, 8%; exports, 3%.


1,2-Difluoroethane, Safety
1,2-Difluoroethane is toxic when inhaled or when it comes into direct contact with the skin. Fluorocarbons are 4 to 5 times heavier than air, so it tends to concentrate in low-lying areas. This increases the risk of inhalation. 1,2-difluoroethane is toxic to humans through several mechanisms. First, because it has a high density, it can displace oxygen in the lungs causing suffocation. In addition, inhaled fluorocarbons causes the myocardium to become more sensitive to catecholamines, which results in deadly cardiac arrhythmias.


1,2-Difluoroethane, Safety
When inhaled by rats, 1,2-difluoroethane is converted to fluoroacetate using cytochrome P450 and then to fluorocitrate both toxic. 100 parts per million in the atmosphere was sufficient to poison rats in 30 minutes and to kill them in four hours. 1,2-Difluoroethane is likely to be similarly toxic to humans.


1,2-Difluoroethane, Environmental fate
1,2-Difluoroethane can enter the environment various ways. One way is through volatilization from rivers and lakes. Henry's law estimates that the volatilization half life from a model river is about 2.4 hours and 3.2 days from a model lake. When 1,2-difluoroethane is released to the environment, it will end up in the atmosphere. Here it is degraded by reaction with hydroxyl radicals and oxygen.


1,2-Difluoroethane, Environmental fate
When catalysed by chlorine atoms and oxidised by nitrogen oxides the end product is HCOF which can decompose further to HF and CO.


1,2-Difluoroethane, Environmental fate
The halflife in air is between 140 and 180 days.


1,2-Difluoroethane, Control
1,2-Difluoroethane is a greenhouse gas when released to the atmosphere. It has a warming equivalent to 140 times that of carbon dioxide. As such it may be controlled by government regulation. The Australian government classifies 1,2-difluoroethane as an exotic synthetic greenhouse gas.


1,2-Difluoroethylene
1,2-Difluoroethylene, also known as 1,2-difluoroethene, is an organofluoride with the molecular formula C2H2F2. It can exist as either of two geometric isomers, cis-1,2-difluoroethylene or trans-1,2-difluoroethylene.


1,2-Difluoroethylene
It is regarded as a hazardous chemical for being toxic by inhalation, and a volatile chemical, and it causes irritation when it comes into contact with the skin and mucous membranes.


1,2-Difluoroethylene, E-Z relative stability
For most 1,2-disubstituted compounds that exhibit cis–trans isomerism, the trans (E) isomer is more stable than the cis (Z) isomer. However, 1,2-difluoroethylene has the opposite situation, with the cis more stable than the trans by 0.9 kcal/mol.


1,2-Diformylhydrazine
1,2-Diformylhydrazine is the chemical compound with the formula N2H2(CHO)2. It is a white, water-soluble solid. A related species is the monoformyl analog, called formic hydrazide (HCON2H3,  ).


1,2-Diformylhydrazine
As verified by X-ray crystallography, it is a planar molecule with N-N, N-C, and C=O distances of 1.38, 1.33 and 1.24 Å, respectively.


1,2-Dihydro-1,2-azaborine
1,2-Dihydro-1,2-azaborine is an aromatic chemical compound with properties intermediate between benzene and borazine. Its chemical formula is C4BNH6. It resembles a benzene ring, except that two adjacent carbons are replaced by nitrogen and boron, respectively.


1,2-Dihydro-1,2-azaborine, Preparation
After decades of failed attempts, the compound was synthesized in 2008 and reported in January 2009.


1,2-Dihydro-1,2-azaborine, Preparation
One of the synthetic steps is a ring-closing metathesis (RCM) reaction:


1,2-Diiodoethane, Preparation and reactions
1,2-Diiodoethane can be prepared by the reaction of ethylene with iodine (I2):


1,2-Diiodoethane, Preparation and reactions
1,2-Diiodoethane is most commonly used in organic synthesis in the preparation of samarium(II) iodide or ytterbium(II) iodide in an inert solvent such as THF.


1,2-Diiodoethane, Spectral properties
In mass spectroscopy, 1,2-diiodoethane exhibits 5 major peaks, with the base peak showing at 155 m/z, which is the loss of one iodine atom (127 m/z).


1,2-Diiodoethylene
1,2-Diiodoethylene, also known as 1,2-diiodoethene, is an organoiodide with the molecular formula C2H2I2. It can exist as either of two geometric isomers, cis-1,2-diiodoethylene or trans-1,2-diiodoethylene.


1,2-Diiodoethylene, E-Z relative stability
Like most cis-trans compounds, the Z isomer (cis) is less stable than the E isomer (trans) by 2 kcal/mol.


1,2-Dimethoxybenzene
1,2-Dimethoxybenzene, commonly known as veratrole, is an organic compound with the formula C6H4(OCH3)2. It is one of three isomers of dimethoxybenzene. It is a colorless liquid, with a pleasant odor and slight solubility in water. It is the dimethyl ether derived from pyrocatechol.


1,2-Dimethoxybenzene, Occurrence
1,2-Dimethoxybenzene is naturally occurring. Its biosynthesis entails the methylation of guaiacol by guaiacol O-methyltransferase. 1,2-Dimethoxybenzene is an insect attractant. Guaiacol O-methyltransferase gene is first scent gene discovered so far in any plant species.


1,2-Dimethoxybenzene, Uses
1,2-Dimethoxybenzene is a building block for the organic synthesis of other aromatic compounds. Veratrole is relatively electron-rich and thus readily undergoes electrophilic substitution.


1,2-Dimethoxybenzene, Uses
An example of the use of veratrole is in the synthesis of Domipizone.


1,2-Dimethoxybenzene, Uses
Veratrole can easily be brominated with NBS to give 4-bromoveratrole.


1,2-Dimethylcyclopropane
1,2-Dimethylcyclopropane is a cycloalkane consisting of a cyclopropane ring substituted with two methyl groups attached to adjacent carbon atoms. It has three stereoisomers, one cis-isomer and a pair of trans-enantiomers, which differ depending on the orientation of the two methyl groups. As with other cyclopropanes, ring tension results in a relatively unstable compound.


1,2-Dimethylcyclopropane
1,2-Dimethylcyclopropane is 1 of 10 structural isomers (cycloalkanes and aliphatic alkenes) which share the general formula of C5H10, the others being cyclopentane, methylcyclobutane, 1,1-dimethylcyclopropane, ethylcyclopropane, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, and 2-methyl-2-butene.


1,2-Dimethyldiborane
1,2-Dimethyldiborane is an organoboron compound with the formula [(CH3)BH2]2. Structurally, it is related to diborane, but with methyl groups replacing terminal hydrides on each boron. It is the dimer of methylborane, CH3BH2, the simplest alkylborane. 1,2-Dimethyldiborane can exist in a cis- and a trans arrangement. 1,2-Dimethyldiborane is an easily condensed, colorless gas that ignites spontaneously in air.


1,2-Dimethyldiborane
An isomer of 1,2-dimethyldiborane is 1,1-dimethyldiborane, known as unsymmetrical dimethyldiborane, which has two methyl groups on one boron atom. Other methylated versions of diborane including methyldiborane, trimethyldiborane, tetramethyldiborane. Trimethylborane exists as a monomer.


1,2-Dimethyldiborane, Preparation
Methylboranes were first prepared by H. I. Schlesinger and A. O. Walker in the 1930s.


1,2-Dimethyldiborane, Preparation
In a more modern synthesis, 1,2-dimethyldiborane is produced by treating lithium methylborohydride with hydrogen chloride:


1,2-Dimethyldiborane, Preparation
Instead of hydrogen chloride, methyl iodide or trimethylsilyl chloride can be used.


1,2-Dimethyldiborane, Preparation
Lithium methylborohydride can be made by treating methylboronic esters with lithium aluminium hydride.


1,2-Dimethyldiborane, Preparation, Miscellaneous routes
Methylboranes arise the reaction of diborane and trimethylborane. This reaction produces 1-methyldiborane, 1,1-dimethyldiborane, 1,1,2-trimethyldiborane, and 1,1,2,2-tetramethyldiborane. By treating monomethyldiborane with ether, dimethyl ether borane (CH3)2O.BH3 leaving methylborane which rapidly dimerises to 1,2-dimethyldiborane. The reaction is complex.


1,2-Dimethyldiborane, Preparation, Miscellaneous routes
Tetramethyl lead reacts with diborane to give a range of methyl-substituted diboranes, ending up at trimethylborane, but including 1,1-dimethyldiborane, and trimethyldiborane. Other products are hydrogen gas and lead metal.


1,2-Dimethyldiborane, Preparation, Miscellaneous routes
Other methods to form methyldiboranes include treating hydrogen with trimethylborane between 80 and 200 °C under pressure, or treating a metal borohydride with trimethylborane in the presence of hydrogen chloride, aluminium chloride or boron trichloride. If the borohydride is sodium borohydride, then methane is a side product. If the metal is lithium, then no methane is produced. dimethylchloroborane and methyldichloroborane are also produced as gaseous products.


1,2-Dimethyldiborane, Preparation, Miscellaneous routes
When Cp2Zr(CH3)2 reacts with diborane, a borohydro group inserts into the zirconium-carbon bond, and methyl diboranes are produced.


1,2-Dimethyldiborane, Preparation, Miscellaneous routes
In ether dimethylcalcium reacts with diborane to produce dimethyldiborane and calcium borohydride:


1,2-Dimethyldiborane, Preparation, Miscellaneous routes
1,2-Dimethyldiborane is produced by the room temperature disproportionation of trimethyldiborane.


1,2-Dimethyldiborane, Physical and spectroscopic properties
cis-1,2-Dimethyldiborane melts at −132.5 °C; trans-1,2-dimethyldiborane melts at −102 °C. The cis-1,2-dimethyldiborane molecule has point group Cs. A trans-1,2-dimethyldiborane molecule has point group C2. Unsymmetrical dimethyldiborane melts at −150.2 °C. Vapour pressure is approximated by Log P = 7.363−(1212/T). The vapour pressure for the symmetrical isomer is given by Log P = 7.523−(1290/T).


1,2-Dimethyldiborane, Physical and spectroscopic properties
Gas chromatography can be used to determine the amounts of the methyl boranes in a mixture. The order of elution are: diborane, monomethyldiborane, trimethylborane, 1,1-dimethyldiborane, 1,2-dimethyldiborane, trimethyldiborane, and last tetramethyldiborane.


1,2-Dimethyldiborane, Physical and spectroscopic properties
The nuclear resonance shift for the bridge hydrogen is 9.55 ppm for the unsymmetrical isomer and 9.73 ppm for the symmetrical isomers, compared to 10.49 for diborane.


1,2-Dimethyldiborane, Reactions
Methylborane shows little tendency to disproportionate (redistribute) at room temperature. It reacts stepwise with alkenes to produce mono and dialkylmethylboranes. More methylated boranes are less stable.


1,2-Dimethyldiborane, Reactions
Symmetrical dimethyldiborane reacts with trimethylamine to yield a solid adduct trimethylamine-methylborane (CH3)3N·BH2CH3.


1,2-Dimethyldiborane, Reactions
When dimethyldiborane is combined with ammonia and heated, B-methyl borazoles are produced. These borazoles can have one, two or three methyl groups substituted on the boron atoms.


1,2-Dimethylethylenediamine
1,2-Dimethylethylenediamine (DMEDA) is the organic compound with the formula (CH3NH)2C2H4. It is a colorless liquid with a fishy odor. It features two secondary amine functional groups.


1,2-Dimethylethylenediamine, Reactions
DMEDA is used as a chelating diamine for the preparation of metal complexes, some of which function as homogeneous catalysts.


1,2-Dimethylethylenediamine, Reactions
The compound is used as a precursor to imidazolidines by condensation with ketones or with aldehydes:


1,2-Dimethylhydrazine
1,2-Dimethylhydrazine, or symmetrical dimethylhydrazine, is the organic compound with the formula (CH3NH)2. It is one of the two isomers of dimethylhydrazine. Both isomers are colorless liquids at room temperature, with properties similar to those of methylamines. 1,2-Dimethylhydrazine is a potent carcinogen that acts as a DNA methylating agent. The compound has no commercial value, in contrast to its isomer, which is used as a rocket fuel.


1,2-Dimethylhydrazine
It is used to induce colon tumors in experimental animals - particularly mice and feline cell samples.


1,2-Dinitrobenzene
1,2-Dinitrobenzene is an organic compound with the formula C6H4(NO2)2. It is one of three isomers of dinitrobenzene. The compound is a white or colorless solid that is soluble in organic solvents. It is prepared from 2-nitroaniline by diazotization and treatment with sodium nitrite in the presence of a copper catalyst.


1,2-Dioleoyl-sn-glycerophosphoethanolamine
1,2-Dioleoyl-sn-glycerophosphoethanolamine is a non-bilayer lipid of the phosphatidylethanolamine class, it adopts non-lamellar reverse hexagonal structures. It forms part of Lipofectamine, a common transfection reagent.


1,2-Dioxane
1,2-Dioxane or o-dioxane is an organic compound with the molecular formula (CH2)4O2, classified as a cyclic peroxide. Its synthesis was reported in 1956 by Criegee and Müller, who prepared it by reacting butane-1,4-diol bis(methanesulfonate) with hydrogen peroxide and distilled it as a colorless liquid. Acids and bases decompose it to gamma-hydroxybutyraldehyde.


1,2-Dioxane
Substituted 1,2-dioxanes have also been prepared, and some have been isolated from natural sources.


1,2-Dioxetane
The chemical substance 1,2-dioxetane  (1,2-dioxacyclobutane) is a heterocyclic organic compound with formula C2O2H4, containing a ring of two adjacent oxygen atoms and two adjacent carbon atoms. It is therefore an organic peroxide, and can be viewed as a dimer of formaldehyde (COH2).


1,2-Dioxetane, Luminescence
In the 1960s, biochemists discovered that some derivatives of 1,2-dioxetane have a fleeting existence as intermediates in the reactions responsible for the bioluminescence in fireflies, glow-worms and other luminescent creatures. The luminescence of glowsticks and luminescent bangles and necklaces involves 1,2-dioxetanedione (C2O4), another dioxetane derivative that decomposes to carbon dioxide. Other dioxetane derivatives are used in clinical analysis, where their light emission (which can be measured even at very low levels) allows chemists to detect very low concentrations of body fluid constituents.


1,2-Dioxetane, Derivatives
The hypothesis could not be proved because these four-membered cyclic peroxides are quite unstable. Then in 1968 the first example of a stable dioxetane derivative was made at the University of Alberta in Edmonton: 3,3,4-trimethyl-1,2-dioxetane, prepared as a yellow solution in benzene. When heated to 333 K, it decomposed smoothly (rather than explosively, as many peroxides do) to acetone and acetaldehyde with the emission of pale blue light.


1,2-Dioxetane, Derivatives
The second example of a dioxetane derivative was made shortly after: the symmetrical compound 3,3,4,4-tetramethyl-1,2-dioxetane, obtained as pale yellow crystals that sublimed even when kept in the refrigerator. Benzene solutions of this compound also decomposed smoothly with the emission of blue light. By adding compounds that normally fluoresce in UV light the colour of the emitted light could be altered.


1,2-Dioxetane, Carbon monoxide
The dioxetane intermediate is capable of generating carbon monoxide and has been explored as a carbon monoxide pro-drug.


1,2-Dioxetane, Carbon monoxide
Peroxidation of the reactive enol of alpha keto acids, such as the tautomer of phenylpyruvic acid at the benzylic carbon, can form a fluorescing 1,2-dioxetane to generate benzaldehyde and oxalic acid. Alternatively, a peroxylactone can form (alpha-keto-beta-peroxylactone) which also forms benzaldehyde but liberates carbon dioxide and carbon monoxide.


1,2-Dioxetanedione
The chemical compound 1,2-dioxetanedione, or 1,2-dioxacyclobutane-3,4-dione, often called peroxyacid ester, is an unstable oxide of carbon (an oxocarbon) with formula C2O4. It can be viewed as a double ketone of 1,2-dioxetane (1,2-dioxacyclobutane), or a cyclic dimer of carbon dioxide.


1,2-Dioxetanedione
In ordinary conditions, it quickly decomposes to carbon dioxide (CO2) even at 180 K (−93.1 °C), but can be detected by mass spectrometry and other techniques.


1,2-Dioxetanedione
1,2-Dioxetanedione is an intermediate in the chemoluminescent reactions used in glowsticks. The decomposition proceeds via a paramagnetic oxalate biradical intermediate.


1,2-Dioxetanedione
Recently it has been found that a high-energy intermediate in one of these reactions (between oxalyl chloride and hydrogen peroxide in ethyl acetate), which is presumed to be 1,2-dioxetanedione, can accumulate in solution at room temperature  (up to a few micromoles at least), provided that the activating dye and all traces of metals and other reducing agents are removed from the system, and the reactions are carried out in an inert atmosphere.


1,2-Dioxin
1,2-Dioxin is a heterocyclic, organic, antiaromatic compound with the chemical formula C4H4O2. It is an isomeric form of 1,4-dioxin (or p-dioxin).


1,2-Dioxin
Due to its peroxide-like characteristics, 1,2-dioxin is very unstable and has not been isolated. Calculations suggest that it would isomerize rapidly into but-2-enedial. Even substituted derivatives are very labile, e.g. 1,4-diphenyl-2,3-benzodioxin. Indeed, in 1990, 3,6-bis(p-tolyl)-1,2-dioxin was wrongly accounted as the first stable derivative. It was subsequently shown that the initial compound was not a derivative of 1,2-dioxin, but a thermodynamically more stable dione.


1,2-Dioxolane
1,2-Dioxolane is a chemical compound with formula C3H6O2, consisting of a ring of three carbon atoms and two oxygen atoms in adjacent positions. Its structural formula could be written as [–(CH2)3–O–O–].


1,2-Dioxolane
The compound is an organic peroxide, specifically an endoperoxide, and a structural isomer of the much more common 1,3-dioxolane, which is often called simply "dioxolane".


1,2-Dioxolane, Synthesis
Synthesis methods for the 1,2-dioxolane core structure include oxidation of cyclopropane derivatives with singlet oxygen or molecular oxygen with a suitable catalyst, the use of autooxidation, nucleophilic displacement with hydrogen peroxide, treatment with mercury(II) nitrate, photolysis of extended π-systems, reaction of a bis-silylperoxide and an alkene, or reaction with a 2-perhydroxy 4-alkene with diethylamine or mercury(II) acetate.


1,2-Dioxolane, Occurrence
Some derivatives occur naturally, for example in Calophyllum dispar and from the seeds of the mamey (Mammea americana). Plakinic acid A (3,5-peroxy 3Z,5Z,7,11-tetramethyl 13-phenyl-8E,12E-tridecadienoic acid) and similar compounds were isolated from sponges of the Plakortis genus. Nardosinone is a sesquiterpene derivative with a 1,2-dioxolane element isolated from the plant Adenosma caeruleum.


1,2-Dioxolane, Uses
Synthetic and natural dioxoloane derivatives have been used or considered  as antimalarial drugs. Plakinic acid A and related compounds showed antifungal action.


1,2-Dithietane
1,2-Dithietane is a dithietane. It is a heterocyclic compound with a four-membered ring. Two sulfur atoms are adjacent, and the molecule is saturated. 1,2-Dithietane has not been produced as of 2000. The combination of ring strain, and lone pairs of electrons, which repel each other, on the sulfur atoms makes the sulfur-sulfur bond too weak to produce the molecule. However a few derivatives are known. 3,4-Diethyl-1,2-dithietane 1,1-dioxide has one sulfur fully oxidised. Dithiatopazine is a tricyclic compound with the -S-S- as a bridge. 1,2-Dithietan-3-one, the ketone of 1,2-dithietane, was produced in 2008 by reacting α-dithiolactone with ethoxycarbonylformonitrile oxide. 4,4 -di-tert-butyl-1,2-dithietan-3-one and the spiro compound 4,4-(2',2',6',6'-tetramethylcyclohexyl)1,2-dithietan-3-one have also been made.


1,2-Dithietane
1,2-Dithietane was claimed to have been made by reacting 1,2-ethanedithiol with iodine, but the major product was an eight-membered ring.


1,2-Dithietane
A reaction of 2,3-dimercapto-1-propanol with 3-methyllumiflavin transiently produced 3-hydroxy-1,2-dithietane. This dithietane polymerised under light, breaking and reforming the S-S bonds to form a long chain -SSCH(OH)CH2-.


1,2-Dithiole
In organosulfur chemistry, a 1,2-dithiole is a type of heterocycle. The parent of this class of compounds is 1,2-dithiacyclopentene. The anticancer drug oltipraz is a dithiole.


1,2-Epoxybutane
1,2-Epoxybutane is an organic compound with the formula CH2(O)CHCH2CH3. It is a chiral epoxide  prepared by oxidation of 1-butene.


1,2-Indandione
1,3-Indandione is an organic compound with the molecular formula C9H6O2. Chemically, it is a vicinal diketone on an indane framework.


1,2-Indandione
1,2-Indandione is used in the first stage of forensic identification of latent fingerprints. It is particularly useful for paper, and for items printed with thermal inks such as receipts. Amino acids left behind by the human hand may be developed into fingerprints by the use of it; the results, photographed with a special filter under a strong yellow-green fluorescent or green laser. It is usually the first method employed in a sequential analysis aimed at the production of evidence of a grade suitable for use in the courtroom.


1,2-Naphthoquinone
1,2-Naphthoquinone or ortho-naphthoquinone is a polycyclic aromatic organic compound with formula C10H6O2. This yellow solid is prepared by oxidation of 1-amino-2-hydroxynaphthalene with ferric chloride.


1,2-Naphthoquinone, Occurrence
This diketone (an ortho-quinone) is a metabolite of naphthalene. It arises from the naphthalene-1,2-oxide.


1,2-Naphthoquinone, Occurrence
It is also found in diesel exhaust particles. The accumulation of this toxic metabolite in rats from doses of naphthalene has been shown to cause eye damage, including the formation of cataracts.


1,2-Octanediol
1,2-Octanediol, also known as caprylyl glycol, is a diol with the molecular formula CH3(CH2)5CHOHCH2OH.


1,2-Octanediol
It is a common component of many creams and ointments, where it is used as a skin conditioning agent. It is also noted to have some antimicrobial (preserving) ability.


1,2-Propanedithiol
1,2-Propanedithiol, sometimes called 1,2-dimercaptopropane, is a thiol with the formula HSCH2CH(SH)CH3. This colorless, intensely odorous liquid is the simplest chiral dithiol. Related dithiols include 1,2-ethanedithiol, 2,3-dimercapto-1-propanesulfonic acid, and 1,3-propanedithiol. It is generated by the addition of H2S to the related episulfide, CH3CHCH2S.


1,2-Wittig rearrangement
A 1,2-Wittig rearrangement is a categorization of chemical reactions in organic chemistry, and consists of a 1,2-rearrangement of an ether with an alkyllithium compound. The reaction is named for Nobel Prize winning chemist Georg Wittig.


1,2-Wittig rearrangement
The intermediate product is an alkoxy lithium salt and the final product an alcohol. When R" is a good leaving group and electron withdrawing functional group such as a cyanide (CN) group, this group is eliminated and the corresponding ketone is formed.


1,2-Wittig rearrangement, Reaction mechanism
The reaction mechanism centers on the formation of a free radical pair with lithium migrating from the carbon atom to the oxygen atom. The R radical then recombines with the ketyl.


1,2-Wittig rearrangement, Reaction mechanism
The alkyl group migrates in the order of thermodynamical stability methyl < primary alkyl < secondary alkyl < tertiary alkyl, this is in line with the radical mechanism. The radical-ketyl pair is short lived and due to a solvent cage effect some isomerizations take place with retention of configuration.


1,2-Wittig rearrangement, Reaction mechanism
With certain allyl aryl ethers a competing reaction takes place. The reaction of allyl phenyl ether 1 with sec-butyllithium at −78 °C gives the lithiated intermediate 2 which on heating to −25 °C only shows the rearranged product 5 but not 4 after trapping the lithium alkoxide with trimethylsilyl chloride. This result rules out a radical-ketyl intermediate 3a in favor of the Meisenheimer complex 3b. Additional evidence for this mechanism is provided by the finding that with a para tert-butyl substituent the reaction is retarded.


1,2-alpha-L-fucosidase
In enzymology, a 1,2-alpha-L-fucosidase (EC ) is an enzyme that catalyzes the chemical reaction


1,2-alpha-L-fucosidase
Thus, the two substrates of this enzyme are methyl-2-alpha-L-fucopyranosyl-beta-D-galactoside and H2O, whereas its two products are L-fucose and methyl beta-D-galactoside.


1,2-alpha-L-fucosidase
This enzyme belongs to the family of hydrolases, specifically those glycosidases that hydrolyse O- and S-glycosyl compounds. The systematic name of this enzyme class is 2-alpha-L-fucopyranosyl-beta-D-galactoside fucohydrolase. Other names in common use include almond emulsin fucosidase, and alpha-(1->2)-L-fucosidase.


1,2-alpha-L-fucosidase, Structural studies
As of late 2007, 4 structures have been solved for this class of enzymes, with PDB accession codes , , , and .


1,2-dehydroreticulinium reductase (NADPH)
In enzymology, a 1,2-dehydroreticulinium reductase (NADPH) (EC ) is an enzyme that catalyzes the chemical reaction


1,2-dehydroreticulinium reductase (NADPH)
Thus, the two substrates of this enzyme are (R)-reticuline and NADP+, whereas its 3 products are 1,2-dehydroreticulinium, NADPH, and H+.


1,2-dehydroreticulinium reductase (NADPH)
This enzyme belongs to the family of oxidoreductases, specifically those acting on the CH-NH group of donors with NAD+ or NADP+ as acceptor. The systematic name of this enzyme class is (R)-reticuline:NADP+ oxidoreductase. This enzyme is also called 1,2-dehydroreticulinium ion reductase. This enzyme participates in alkaloid biosynthesis i.


1,2-diacylglycerol 3-glucosyltransferase
In enzymology, a 1,2-diacylglycerol 3-glucosyltransferase (EC ) is an enzyme that catalyzes the chemical reaction


1,2-diacylglycerol 3-glucosyltransferase
Thus, the two substrates of this enzyme are UDP-glucose and 1,2-diacylglycerol, whereas its two products are UDP and 3-D-glucosyl-1,2-diacylglycerol.


1,2-diacylglycerol 3-glucosyltransferase
This enzyme belongs to the family of glycosyltransferases, specifically the hexosyltransferases. The systematic name of this enzyme class is UDP-glucose:1,2-diacylglycerol 3-D-glucosyltransferase. Other names in common use include UDP-glucose:diacylglycerol glucosyltransferase, UDP-glucose:1,2-diacylglycerol glucosyltransferase, uridine diphosphoglucose-diacylglycerol glucosyltransferase, and UDP-glucose-diacylglycerol glucosyltransferase. This enzyme participates in glycerolipid metabolism.


1,2-dihydrovomilenine reductase
In enzymology, a 1,2-dihydrovomilenine reductase (EC ) is an enzyme that catalyzes the chemical reaction


1,2-dihydrovomilenine reductase
Thus, the two substrates of this enzyme are 17-O-acetylnorajmaline and NADP+, whereas its 3 products are 1,2-dihydrovomilenine, NADPH, and H+.


1,2-dihydrovomilenine reductase
This enzyme belongs to the family of oxidoreductases, specifically those acting on the CH-CH group of donor with NAD+ or NADP+ as acceptor. The systematic name of this enzyme class is 17-O-acetylnorajmaline:NADP+ oxidoreductase. This enzyme participates in indole and ipecac alkaloid biosynthesis.


1,2-dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate dehydrogenase
In enzymology, a 1,2-dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate dehydrogenase (EC ) is an enzyme that catalyzes the chemical reaction


1,2-dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate dehydrogenase
Thus, the two substrates of this enzyme are 1,2-dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate and NAD+, whereas its 3 products are 3-methylcatechol, NADH, and CO2.


1,2-dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate dehydrogenase
This enzyme belongs to the family of oxidoreductases, specifically those acting on the CH-CH group of donor with NAD+ or NADP+ as acceptor. The systematic name of this enzyme class is 1,2-dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate:NAD+ oxidoreductase (decarboxylating). This enzyme participates in toluene and xylene degradation.


1,2-dihydroxynaphthalene dioxygenase
1,2-dihydroxynaphthalene dioxygenase (EC , 1,2-DHN dioxygenase, DHNDO, 1,2-dihydroxynaphthalene oxygenase, 1,2-dihydroxynaphthalene:oxygen oxidoreductase) is an enzyme with systematic name naphthalene-1,2-diol:oxygen oxidoreductase. This enzyme catalyses the following chemical reaction


1,2-rearrangement
A 1,2-rearrangement or 1,2-migration or 1,2-shift or Whitmore 1,2-shift is an organic reaction where a substituent moves from one atom to another atom in a chemical compound. In a 1,2 shift the movement involves two adjacent atoms but moves over larger distances are possible. In the example below the substituent R moves from carbon atom C2 to C3.


1,2-rearrangement
The rearrangement is intramolecular and the starting compound and reaction product are structural isomers. The 1,2-rearrangement belongs to a broad class of chemical reactions called rearrangement reactions.


1,2-rearrangement
A rearrangement involving a hydrogen atom is called a 1,2-hydride shift. If the substituent being rearranged is an alkyl group, it is named according to the alkyl group's anion: i.e. 1,2-methanide shift, 1,2-ethanide shift, etc.


1,2-rearrangement, Reaction mechanism
A 1,2-rearrangement is often initialised by the formation of a reactive intermediate such as:


1,2-rearrangement, Reaction mechanism
The driving force for the actual migration of a substituent in step two of the rearrangement is the formation of a more stable intermediate. For instance a tertiary carbocation is more stable than a secondary carbocation and therefore the SN1 reaction of neopentyl bromide with ethanol yields tert-pentyl ethyl ether.


1,2-rearrangement, Reaction mechanism
Carbocation rearrangements are more common than the carbanion or radical counterparts. This observation can be explained on the basis of Hückel's rule. A cyclic carbocationic transition state is aromatic and stabilized because it holds 2 electrons. In an anionic transition state on the other hand 4 electrons are present thus antiaromatic and destabilized. A radical transition state is neither stabilized or destabilized.


1,2-rearrangement, Reaction mechanism
The most important carbocation 1,2-shift is the Wagner–Meerwein rearrangement. A carbanionic 1,2-shift is involved in the benzilic acid rearrangement.


1,2-rearrangement, Radical 1,2-rearrangements
The first radical 1,2-rearrangement reported by Heinrich Otto Wieland in 1911 was the conversion of bis(triphenylmethyl)peroxide 1 to the tetraphenylethane 2.


1,2-rearrangement, Radical 1,2-rearrangements
The reaction proceeds through the triphenylmethoxyl radical A, a rearrangement to diphenylphenoxymethyl C and its dimerization. It is unclear to this day whether in this rearrangement the cyclohexadienyl radical intermediate B is a transition state or a reactive intermediate as it (or any other such species) has thus far eluded detection by ESR spectroscopy.


1,2-rearrangement, Radical 1,2-rearrangements
An example of a less common radical 1,2-shift can be found in the gas phase pyrolysis of certain polycyclic aromatic compounds. The energy required in an aryl radical for the 1,2-shift can be high (up to 60 kcal/mol or 250 kJ/mol) but much less than that required for a proton abstraction to an aryne (82 kcal/mol or 340 kJ/mol). In alkene radicals proton abstraction to an alkyne is preferred.


1,227 QI Facts to Blow Your Socks Off
1,227 QI Facts To Blow Your Socks Off is the sixth in a series of books based on the intellectual British panel game QI, written by series-creator John Lloyd, director of research John Mitchinson, and chief researcher James Harkin. Published on 1 November 2012 (9 September 2013 in the US), it is a trivia book containing 1,227 facts collected during the making of the series, which had been ten years in the making at the time of publication.


1,227 QI Facts to Blow Your Socks Off, Publication history
Lloyd said in an interview with The Daily Telegraph: "This book is like a set of haiku. I think it's the best thing we've ever done. It has purity and simplicity."


1,227 QI Facts to Blow Your Socks Off, Structure
The book contains lists of facts, normally four per page. All the sources for the facts are listed online on the QI website. Other than Lloyd, Mitchinson and Harkin, credit for authorship is also given to QI researchers (also known as "Elves") Anne Miller, Andy Murray and Alex Bell.


1,227 QI Facts to Blow Your Socks Off, Structure
The reason for the number of facts being 1,227, according to Lloyd and Mitchinson, was that they had originally planned to have 1,000 facts and when they wrote down the list containing all the facts that would go in the book, they discovered that they had gone past the number, to 1,227.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides
1,3,2,4-Dithiadiphosphetane 2,4-disulfides are a class of four-membered ring compounds which contain a P2S2 ring, many of these compounds are able to act as sources of the dithiophosphine ylides. The most well known example of this class of compound is Lawesson's reagent.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides
Other examples of this class of compound have been made; many inorganic chemists are now using Fc2P2S4 (Fc = ferrocene) as a starting material in reactions investigating the general chemistry of the 1,3,2,4-dithiadiphosphetane 2,4-disulfides, one reaction for this is that the Fc2P2S4 compound and all its derivatives are red which make column chromatography of the products more easy. Also the ferrocenyl groups provide an electrochemical handle which provide another means of investigating the properties of the products.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Examples
While several different routes to the 1,3,2,4-dithiadiphosphetane 2,4-disulfides exist the most commonly used is the electrophilic aromatic substitution reaction of an arene with P4S10. An alternative reaction is the reaction of a thiol with P4S10 to form a substance like the Davy reagent. The Davy reagent is identical to Lawesson's reagent except in place of the para-methoxyphenyl groups it has aryl sulfide groups. While the Davy reagent is more soluble than the Lawesson's reagent it is likely that the very vile nature of the thiol starting material is likely to make the synthesis of this compound not worth the trouble.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Examples
In both the patent and academic chemical literature are examples of 1,3,2,4-dithiadiphosphetane 2,4-disulfides with higher solubilities. These highly soluble versions of Lawesson's reagent are created by the reaction of P4S10 with aryl ethers which are different from anisole. For instance butoxybenzene and 2-tert-butylanisole have both been reacted to form more soluble thionation reagents of the 1,3,2,4-dithiadiphosphetane 2,4-disulfide class.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Examples
An important subclass of these compounds are the naphthalen-1,8-diyl 1,3,2,4-dithiadiphosphetane 2,4-disulfides; these are intellectually interesting because the two dithiophosphine ylides are fixed together in space by the rigid naphthalene unit. The reactivity of these compounds is very different from that of 1,3,2,4-dithiadiphosphetane 2,4-disulfides.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Reactions
The dithiophosphine ylides are normally attacked at the phosphorus atom by a nucleophile, for instance the reaction of an alkoxide, phenolate, alcohol or phenol with a 1,3,2,4-dithiadiphosphetane 2,4-disulfide can form a new compound with a phosphorus-oxygen bond. Such a reaction has been used in the formation of metal binding agents and in the synthesis of insecticides.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Reactions
The reaction of an electrophile with 1,3,2,4-dithiadiphosphetane 2,4-disulfides is less common, but the reaction of an alkyl halide with a 1,3,2,4-dithiadiphosphetane 2,4-disulfide forms a new compound with a sulfur-carbon bond and a phosphorus-halide bond. Such a compound could act as an acetylcholinesterase inhibitor in insects, but in order to make a better insecticide it would be best to convert the halide to another leaving group which would form a less water sensitive product. For instance the reaction of para-nitrophenolate would form a compound similar to parathion.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Reactions
Lawesson's reagent has been used as a starting material for a herbicide by reaction with a 1-alkoxy-2,3-dihydroxy propane. This formed a compound which could be used to kill plants. This reaction of a 1,2-diol with lawesson's reagent results in a symmetric breaking of the P2S2 ring, both halves of the lawesson's reagent end up being converted to the same product.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Reactions
A different type of ring breaking reaction can occur when LR is reacted with a metal compounds such as a platinum dichloride bis-phosphine complex, in this case one molecule of MeOC6H4P(S)Cl2 is formed as a side product to the platinum complex ([Pt(S2P(S)C6H4OMe)(PR3)2]).


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Reactions
Lawesson's reagent can be used as a dehydrating reagent, for example it has been used to convert a β-aminoamide into an imidazoline.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Reactions
Another useful reaction of LR is the conversion of a 1,4-diketone into a thiophene ring, this reaction can be done with P4S10 but a much higher temperature would be required to make it work with P4S10.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Reactions
It was claimed in a German patent that the reaction of 1,3,2,4-dithiadiphosphetane 2,4-disulfides with dialkyl cyanamides formed plant protection agents which contained six-membered (P-N=C-N=C-S-) rings. It has been proven in recent times by the reaction of diferrocenyl 1,3,2,4-dithiadiphosphetane 2,4-disulfide (and Lawesson's reagent) with dimethyl cyanamide that in fact a mixture of several different phosphorus containing compounds is formed. Depending on the concentration of the dimethyl cyanamide in the reaction mixture either a different six membered ring compound (P-N=C-S-C=N-) or a nonheterocylic compound (FcP(S)(NR2)(NCS)) is formed as the major product, the other compound is formed as a minor product.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Reactions
In addition small traces of other compounds are also formed in the reaction. It is unlikely that the ring compound (P-N=C-S-C=N-) {or its isomer} would act as a plant protection agent, but (FcP(S)(NR2)(NCS)) compounds can act as nerve poisons in insects. These compounds bearing terminal sulfur atoms on the phosphorus atom are much less toxic than the compounds (such as sarin, VX and tetraethyl pyrophosphate) which have an oxygen in place of this terminal sulfur.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Reactions
This is because the P=S compound is not active as an acetylcholinesterase inhibitor in either mammals or insects, in mammals the animals metabolism tends to remove lipophilic side groups from the phosphorus atom while an insect tends to oxidise the compound so removing the terminal sulfur and replacing it with a terminal oxygen which causes the compound to be more able to act as an acetylcholinesterase inhibitor.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Reactions
The dithiophosphine ylides of LR and related compounds can react with strained alkenes, for example the bicyclic norbornadiene reacts with Fc2P2S4 to form a compound with a PSC2 ring. Unlike small rings containing only first row elements such as carbon, nitrogen and oxygen the small rings containing more heavy elements such as sulfur and selenium are more stable with regards to ring opening. Hence, the rings such as PSC2 are much more stable than things like epoxides.


1,3,2,4-Dithiadiphosphetane 2,4-disulfides, Reactions
A selenium version of this ring type has been made, one notable example has been named Woollins' reagent and is Ph2P2Se4, this is made by the reaction of (PhP)5 with selenium metal. The solubility of this compound is very low but the group of Prof John Derek Woollins have published some reactions of this compound. For instance the reaction of Woollins' reagent (WR) with a dialkyl cyanamide has been found to form a bicyclic PC2N2Se3 system.


1,3,3,3-Tetrafluoropropene
1,3,3,3-Tetrafluoropropene (HFO-1234ze(E), R-1234ze) is a hydrofluoroolefin. It was developed as a "fourth generation" refrigerant to replace fluids such as R-134a, as a blowing agent for foam and aerosol applications, and in air horns and gas dusters. The use of R-134a is being phased out because of its high global-warming potential. HFO-1234ze(E) itself has zero ozone-depletion potential (ODP=0), a very low global-warming potential (GWP < 1 ), even lower than CO2, and it is classified by ANSI/ASHRAE as class A2L refrigerant (lower flammability and lower toxicity).


1,3,3,3-Tetrafluoropropene
In open atmosphere however, HFO-1234ze actually might form HFC-23 as one of its secondary atmospheric breakdown products. HFC-23 is a very potent greenhouse gas with a GWP100 of 14,800. The secondary GWP of R-1234ze would then be in the range of 1,400±700 considering the amount of HFC-23 which may form from HFO-1234ze in the atmosphere. Besides the global warming potential, when HFOs decompose in the atmosphere, trifluoroacetic acid (TFA(A)) is formed, which also remains in the atmosphere for several days. The trifluoroacetic acid then forms trifluoroacetate (TFA), a salt of trifluoroacetic acid, in water and on the ground. Due to its high polarity and low degradability, it is difficult to remove TFA from drinking water (ICPR 2019).


1,3,3,3-Tetrafluoropropene, Uses
The increasing concerns about global warming and the related possible undesirable climate effects have led to an increasing agreement in developed countries for the reduction of greenhouse gas emissions. Given the relatively high global warming potential (GWP) of most of the hydro-fluoro-carbons (HFCs), several actions are ongoing in different countries to reduce the use of these fluids. For example, the European Union’s recent F-Gas regulation specifies the mandatory GWP values of the refrigerants to be used as working fluids in almost all air conditioners and refrigeration machines beginning in 2020.


1,3,3,3-Tetrafluoropropene, Uses
Several types of possible replacement candidates have been proposed so far, both synthetic and natural. Among the synthetic options, hydro-fluoro-olefins (HFOs) are the ones appearing most promising thus far.


1,3,3,3-Tetrafluoropropene, Uses
HFO-1234ze(E) has been adopted as a working fluid in chillers, heat pumps, and supermarket refrigeration systems.


1,3,3,3-Tetrafluoropropene, Uses
It has been demonstrated that HFO-1234ze(E) can not be considered as a drop-in replacement of HFC-134a. In fact, from a thermodynamic point-of-view, it can be stated that:


1,3,3,3-Tetrafluoropropene, Uses
– The theoretical coefficients of performance of HFO-1234ze(E) is slightly lower than HFC-134a one;


1,3,3,3-Tetrafluoropropene, Uses
– HFO-1234ze(E) has a different volumetric cooling capacity when compared to HFC-134a.


1,3,3,3-Tetrafluoropropene, Uses
– HFO-1234ze(E) has saturation pressure drops higher than HFC-134a during two-phase heat transfer under the constraint of achieving the same heat transfer coefficient.


1,3,3,3-Tetrafluoropropene, Uses
So, from a technological point-of-view, modifications to the condenser and evaporator designs and to compressor displacement are needed to achieve the same cooling capacity and energetic performance of HFC-134a.


1,3,3-Trinitroazetidine
1,3,3-Trinitroazetidine (TNAZ) is a highly energetic heterocyclic compound that has been considered as a potential replacement for TNT because of its low melting point (101 °C) and good temperature stability (up to 240 °C). TNAZ was first synthesized by Archibald et al. in 1983 in work published in 1990. Several synthesis routes are known and bulk production of several hundred kilogram batches has been demonstrated at Los Alamos National Laboratory.


1,3,3-Trinitroazetidine, Properties
TNAZ forms pale yellow crystals with a melting point of 101 °C. The compound crystallizes in an orthorhombic lattice with the space group Pbca. Thermolysis occurs starting around 240 °C - 250 °C with decomposition products that include nitrogen dioxide, nitric oxide, nitrous acid, carbon dioxide and formaldehyde. As far as energetic properties, it is roughly 30% more energetic than TNT and has a heat of explosion of ~6343 kJ/kg, a detonation velocity of ~9000 m/s, and a detonation pressure of 36.4 GPa.


1,3,4-Oxadiazole
1,3,4-Oxadiazole is a nitrogen and oxygen containing heterocycle, and one of the four isomers of oxadiazole.


1,3,4-Oxadiazole, Derivatives
1,3,4-Oxadiazole itself is not commonly used in organic chemistry, but many of its derivatives are important. For example, raltegravir is an HIV drug which contains an 1,3,4-oxadiazole ring. Other pharmaceutical drugs containing the 1,3,4-oxadiazole ring include fenadiazole, zibotentan, and tiodazosin.


1,3,4-Oxadiazole, Derivatives
1,3,4-Oxadiazole derivatives can be synthesized in a variety of ways. One pathway is from oxidation of tetrazoles in the presence of aldehydes. Similarly, the reaction of tetrazoles with acyl chlorides provides oxadiazoles. Both methods involve the release of N2.


1,3,5-Triaza-7-phosphaadamantane
1,3,5-Triaza-7-phosphaadamantane (PTA) is a chemical compound with the formula C6H12N3P, a product of the substitution of a nitrogen atom of hexamethylenetetramine with a phosphorus atom. It is soluble in water, methanol, trichloromethane, acetone, ethanol and DMSO, insoluble in hydrocarbon solvent. As a reagent in organic synthesis, it is used as a ligand for transition metal complexes and as a catalyst for Baylis–Hillman reactions.


1,3,5-Triaza-7-phosphaadamantane, Preparation
Hexamethylenetetramine reacts with tetrakis(hydroxymethyl)phosphonium chloride, sodium hydroxide and formaldehyde in water to obtain the product.


1,3,5-Triazido-2,4,6-trinitrobenzene
1,3,5-Triazido-2,4,6-trinitrobenzene, also known as TATNB (triazidotrinitrobenzene) and TNTAZB (trinitrotriazidobenzene), is an aromatic high explosive composed of a benzene ring with three azido groups (-N3) and three nitro groups (-NO2) alternating around the ring, giving the chemical formula C6(N3)3(NO2)3. Its velocity of detonation is 7,350 meters per second, comparable to TATB (triaminotrinitrobenzene).


1,3,5-Triazido-2,4,6-trinitrobenzene, Preparation
The compound was first synthesized in 1924 by Oldřich Turek. It can be prepared by the reaction of 1,3,5--trichloro-2,4,6-trinitrobenzene with sodium azide, which is obtained from the nitration of 1,3,5-trichlorobenzene with nitric acid and sulfuric acid.


1,3,5-Triazido-2,4,6-trinitrobenzene, Properties, Physical properties
1,3,5-Triazido-2,4,6-trinitrobenzene forms yellow crystalline solids that melt at 131 °C. The crystals are monoclinic with space group P21/c. Its formation is highly endothermic, with an enthalpy of formation of 765.8 kJ/mol and an enthalpy of combustion of 3200 kJ/mol.


1,3,5-Triazido-2,4,6-trinitrobenzene, Properties, Chemical Properties
Even at low temperatures, the compound slowly decomposes by giving off nitrogen gas, converting into benzotrifuroxan. This reaction proceeds quantitatively within 14 hours at 100 °C. As a solution in m-xylene, first order kinetics were observed for the decomposition, with a half-life of 340 minutes at 70 °C, 89 minutes at 80 °C, and 900 seconds at 100 °C.


1,3,5-Triazine
1,3,5-triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. S-triazine—the "symmetric" isomer—and its derivatives are useful in a variety of applications.


1,3,5-Triazine, Preparation
Symmetrical 1,3,5-triazines are prepared by trimerization of certain nitriles such as cyanogen chloride or cyanimide. Benzoguanamine (with one phenyl and 2 amino substituents) is synthesised from benzonitrile and dicyandiamide. In the Pinner triazine synthesis  (named after Adolf Pinner) the reactants are an alkyl or aryl amidine and phosgene. Insertion of an N-H moiety into a hydrazide by a copper carbenoid, followed by treatment with ammonium chloride also gives the triazine core.


1,3,5-Triazine, Preparation
Amine-substituted triazines called Guanamines are prepared by the condensation of cyanoguanidine with the corresponding nitrile:


1,3,5-Triazine, Applications
As a reagent in organic synthesis, s-triazine is used as the equivalent of hydrogen cyanide (HCN). Being a solid (vs a gas for HCN), triazine is sometimes easier to handle in the laboratory. One application is in the Gattermann reaction, used to attach the formyl group to aromatic substrates.


1,3,5-Triazine, Applications, Triazine derivatives
N- and C-substituted triazines are used industrially. The most common derivative of 1,3,5-triazine is 1,3,5-triazine-2,4,6-triamine, commonly known as melamine or cyanuramide. Another important derivative is 1,3,5-triazine-2,4,6-triol better known as cyanuric acid.


1,3,5-Triazine, Applications, Triazine derivatives
2,4,6-Trichloro-1,3,5-triazine (cyanuric chloride) is the starting point for the manufacture of many herbicides such as Simazine and atrazine. Chlorinated triazines are the basis of an important family of reactive dyes, which are covalently attached to cellulosic materials.


1,3,5-Trichlorobenzene
1,3,5-Trichlorobenzene is an organochlorine compound. It is one of the three isomers of trichlorobenzene. Being more symmetrical than the other isomers, it exists as colourless crystals whereas the other isomers are liquids at room temperature.


1,3,5-Trichlorobenzene
It is not formed upon chlorination of benzene. Instead it is prepared by the Sandmeyer reaction from 3,5-dichloroaniline.


1,3,5-Triethylbenzene
1,3,5-Triethylbenzene is a chemical compound of the group of aromatic hydrocarbons.


1,3,5-Triethylbenzene, Preparation
1,3,5-Triethylbenzene can be prepared by a Friedel-Crafts alkylation of benzene with ethyl bromide in presence of aluminum chloride.


1,3,5-Triethylbenzene, Properties
1,3,5-Triethylbenzene is a flammable, hard to ignite, colorless liquid that is almost insoluble in water. The refractive index is 1.495


1,3,5-Triethylbenzene, Uses
1,3,5-Triethylbenzene can be used in synthesis of a series of di- and trinucleating ligands.


1,3,5-Triethylbenzene, Safety notes
The vapour of 1,3,5-Triethylbenzene can form an explosive mixture with air (flash point: 76 °C).


1,3,5-Triheptylbenzene
1,3,5-Triheptylbenzene (also called sym-triheptylbenzene) is an aromatic organic compound with a chemical formula C27H48 and molar mass 372.67 g/mol. It can be prepared by the hydrogenation reduction reaction of 1,1',1''-(benzene-1,3,5-triyl)tris(heptan-1-one). Alternatively, 1-nonyne trimerizes to 1,3,5-triheptylbenzene when catalyzed by rhodium trichloride.


1,3,5-Trimethyl-1,3,5-triazacyclohexane
1,3,5-Trimethyl-1,3,5-triazacyclohexane is an organic compound with the formula (CH3NCH2)3. It is a colorless liquid that is soluble in many organic solvents. Structurally, it is one of several related hexahydro-1,3,5-triazines, which typically result from the condensation reaction of amines and formaldehyde.


1,3,5-Trimethyl-1,3,5-triazacyclohexane
It undergoes deprotonation by butyllithium to give a reagent that serves as a source of the formyl anion.


1,3,5-Trinitrobenzene
1,3,5-Trinitrobenzene is an organic compound with the formula C6H3(NO2)3. It is one of three trinitrated benzene-derivatives. A pale yellow solid, the compound is highly explosive.


1,3,5-Trinitrobenzene, Explosive properties
1,3,5-Trinitrobenzene is a high explosive. It is moderately explosive in liquid form and extremely explosive in its dry powder form. It will detonate under strong shock. High temperatures, whether by sudden heating of any quantity, or by the accumulation of heat when large quantities are burning, will also cause detonation.


1,3,5-Trinitrobenzene, Uses and applications
Trinitrobenzene is more explosive than TNT, but too expensive. It is primarily used as a high explosive compound for commercial mining and military applications. It has also been used as a narrow-range pH indicator, an agent to vulcanize natural rubber, and a mediating agent to mediate the synthesis of other explosive compounds.


1,3,5-Trinitrobenzene, Safety precautions
It is an extremely powerful oxidizing agent which may cause violent reaction with reducing materials.


1,3,5-Trioxane
1,3,5-Trioxane, sometimes also called trioxane or trioxin, is a chemical compound with molecular formula C3H6O3. It is a white solid with a chloroform-like odor. It is a stable cyclic trimer of formaldehyde, and one of the three trioxane isomers; its molecular backbone consists of a six-membered ring with three carbon atoms alternating with three oxygen atoms.


1,3,5-Trioxane, Production
Trioxane can be obtained by the acid-catalyzed cyclic trimerization of formaldehyde in concentrated aqueous solution.


1,3,5-Trioxane, Uses
Trioxane is often used interchangeably with formaldehyde and with paraformaldehyde. It is a precursor for the production of polyoxymethylene plastics, of which about one million tons per year are produced. Other applications exploit its tendency to release formaldehyde. As such it is used as a binder in textiles, wood products, etc. Trioxane is combined with hexamine and compressed into solid bars to make hexamine fuel tablets, used by the military and outdoorsmen as a cooking fuel.


1,3,5-Trioxane, Uses
In the laboratory, trioxane is used as an anhydrous source of formaldehyde.


1,3,5-Trioxanetrione
The chemical compound 1,3,5-trioxanetrione, or 1,3,5-trioxacyclohexane-2,4,6-trione is an unstable oxide of carbon with formula C3O6. It can be considered a cyclic trimer of carbon dioxide (CO2) or as a triple ketone of 1,3,5-trioxane (1,3,5-trioxacyclohexane). Trioxanetrione has been synthesized but is exceedingly unstable, with a half-life of approximately 40 min at −40 °C. It decomposes to give carbon dioxide.


1,3,5-Trithiane
1,3,5-Trithiane is the chemical compound with the formula (CH2S)3. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene bridges and thioether groups. It is prepared by treatment of formaldehyde with hydrogen sulfide.


1,3,5-Trithiane
Trithiane is a building block molecule in organic synthesis, being a masked source of formaldehyde. In one application, it is deprotonated with organolithium reagents to give the lithium derivative, which can be alkylated.


1,3,5-Trithiane
Trithiane is the dithioacetal of formaldehyde. Other dithioacetals undergo similar reactions to the above.


1,3,5-Trithiane
It is also a precursor to other organosulfur reagents. For example, chlorination in the presence of water affords the chloromethyl sulfonyl chloride:


1,3,5-Trithiane, Trithianes
Trithiane is the parent of a class of heterocycles called trithianes, that formally result from substitution of various monovalent groups for one or more of the hydrogen atoms. The species often arise from thiation of ketones and aldehydes. The incipient thioketones and thioaldehydes undergo trimerization. One example is 2,2,4,4,6,6-hexamethyl-1,3,5-trithiane, or trithioacetone, the trimer of thioacetone (propane-2-thione). Alternatively 1,3,5-trithiane can be deprotonated and alkylated to afford (SCH2)n(SCHR)3-n.


1,3,6-Trigalloyl glucose
1,3,6-Trigalloyl glucose is a gallotannin. It can be found in Paeonia lactiflora and Terminalia chebula.


1,3,7-Trimethyluric acid
1,3,7-Trimethyluric acid, also referred to as trimethyluric acid and 8-oxy-caffeine, is a purine alkaloid that is produced in some plants and occurs as a minor metabolite of caffeine in humans. The enzymes that metabolize caffeine into 1,3,7-trimethyluric acid in humans include CYP1A2, CYP2E1, CYP2C8, CYP2C9, and CYP3A4.


1,3,8-Trihydroxyanthraquinone
1,3,8-Trihydroxyanthraquinone is an organic compound. It is one of many trihydroxyanthraquinone isomers, formally derived from anthraquinone by replacement of three hydrogen atoms by hydroxyl (OH) groups.


1,3,8-Trihydroxyanthraquinone
The compound occurs in some microorganisms and in alcoholic extracts of the wood of the South American plant Senna reticulata (mangerioba grande or maria mole in Portuguese), used in the local folk medicine for liver problems and rheumatism. The extract also contained, among other products chrysophanol (1,8-dihydroxy-3-methylanthraquinone), physcion (1,8-dihydroxy-3-methyl-6-methoxyanthraquinone), aloe-emodin (3-carbinol-1,8-dihydroxyanthraquinone), lunatin (3-methoxy-1,6,8-trihydroxyanthraquinone), emodin (6-methyl-1,3,8-trihydroxyanthraquinone), and chrysophanol-10,10'-bianthrone.


1,3,8-Trihydroxyanthraquinone
The substance is soluble in ethanol and chloroform but not in n-hexane, and melts at 283 °C.


1,3-BAC
1,3 BAC chemically 1,3-bis(aminomethyl) cyclohexane is an organic molecule belonging to the sub class cycloaliphatic amine. It has the CAS Registry Number of 2579-20-6. Its key use is as an epoxy resin curing agent.


1,3-BAC, Manufacture
It has been produced commercially as part of a mixture with the 1,4 derivative. The primary route of manufacture is by catalytic hydrogenation of m-Xylylenediamine usually called MXDA.


1,3-BAC, Uses
Like most amines it maybe used as an epoxy curing agent. However, the presence of the amino group also means it can be used in polyurethane chemistry by reacting with isocyanates. In this case a polyurea would be produced. It may also be reacted with phosgene (phosgenation) to produce an isocyanate.


1,3-Benzodioxole
1,3-Benzodioxole (1,2-methylenedioxybenzene) is an organic compound with the formula C6H4O2CH2. The compound is classified as benzene derivative and a heterocyclic compound containing the methylenedioxy functional group. It is a colorless liquid.


1,3-Benzodioxole
Although benzodioxole is not particularly important, many related compounds containing the methylenedioxyphenyl group are bioactive, and thus are found in pesticides and pharmaceuticals.


1,3-Benzodioxolyl-N-ethylbutanamine
Ethylbenzodioxolylbutanamine (EBDB; Ethyl-J) is a lesser-known entactogen, stimulant, and psychedelic. It is the N-ethyl analogue of benzodioxylbutanamine (BDB; "J"), and also the α-ethyl analogue of methylenedioxyethylamphetamine (MDEA; "Eve").


1,3-Benzodioxolyl-N-ethylbutanamine
EBDB was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage consumed was 90 mg, and the duration is unknown. EBDB produced few to no effects at the dosage range tested in PiHKAL, but at higher doses of several hundred milligrams it produces euphoric effects similar to those of methylbenzodioxylbutanamine (MBDB; "Eden", "Methyl-J"), although milder and shorter lasting.


1,3-Benzodioxolyl-N-ethylbutanamine
Very little data exists about the pharmacological properties, metabolism, and toxicity of EBDB.


1,3-Benzodioxolyl-N-ethylpentanamine
N-Ethyl-1,3-benzodioxolylpentanamine (EBDP; Ethyl-K; 3,4-methylenedioxy-N-ethyl-α-propylphenethylamine) is a psychoactive drug and member of the phenethylamine chemical class which acts as an entactogen, psychedelic, and stimulant. It is the N-ethyl analog of 1,3-benzodioxolylpentanamine (BDP; K). Ethyl-K was first synthesized by Alexander Shulgin. In his book PiHKAL ("Phenethylamines i Have Known And Loved"), the minimum dosage is listed as 40 mg and the duration is unknown. Very little is known about the pharmacology, pharmacokinetics, effects, and toxicity of Ethyl-K.


1,3-Benzodioxolyl-N-ethylpentanamine, Legality, United Kingdom
This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.


1,3-Benzodioxolyl-N-methylpentanamine
N-Methyl-1,3-benzodioxolylpentanamine (MBDP; Methyl-K, UWA-091), also known as 3,4-methylenedioxy-α-propyl-N-methylphenethylamine, is a psychoactive drug of the phenethylamine chemical class. It is the N-methyl analogue of 1,3-benzodioxolylpentanamine (BDP; K). Methyl-K was first synthesized by Alexander Shulgin ("Sasha" Shulgin). In his book PiHKAL ("Phenethylamines i Have Known And Loved"), the minimum dosage is listed as 100 mg, and the duration is unknown. Very little is known about the pharmacology, pharmacokinetics, effects, and toxicity of Methyl-K.


1,3-Benzodioxolyl-N-methylpentanamine, Legality, United Kingdom
This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.


1,3-Benzodioxolylbutanamine
1,3-Benzodioxolylbutanamine (also known as 3,4-methylenedioxybutanphenamine, MDB, BDB, J, and 3,4-methylenedioxy-α-ethylphenethylamine) is an entactogenic drug of the phenethylamine chemical class. It is the α-ethyl analog of MDPEA and MDA and the methylenedioxy analogue of α-ethylphenethylamine.


1,3-Benzodioxolylbutanamine
BDB was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 150–230 mg and the duration is listed as 4–8 hours. BDB produces entactogenic, MDMA-like effects. Although pleasant and euphoric, BDB is also fairly sedating and some users feel that the lack of stimulant effect makes it less enjoyable than other similar drugs. Additional side effects associated with BDB include nystagmus and dizziness. Very little data exists about the pharmacological properties, metabolism, and toxicity of BDB.


1,3-Benzodioxolylbutanamine
Animal studies and anecdotal reports show that BDB is a slightly more potent serotonin releasing agent than its methylated sister compound methylbenzodioxylbutanamine (MBDB; "Eden", "Methyl-J"). However, it is more commonly known as a metabolite of the N-alkylated analogues MBDB and ethylbenzodioxylbutanamine (EBDB; "Ethyl-J") which have appeared in methylenedioxymethamphetamine (MDMA; "Ecstasy", "Adam", "Empathy", "Molly", "E", "X", "XTC") tablets.


1,3-Benzodioxolylbutanamine
Although BDB itself has not been reported as being sold as "Ecstasy", urine analysis of "Ecstasy" users suggest that this drug may have appeared as a street drug, although it is unclear whether the positive urine test for BDB resulted from consumption of BDB itself or merely as a metabolite of MBDB.


1,3-Beta-glucan synthase
1,3-Beta-glucan synthase is a glucosyltransferase enzyme involved in the generation of beta-glucan in fungi. It serves as a pharmacological target for antifungal drugs such as caspofungin, anidulafungin, and micafungin, deemed 1,3-Beta-glucan synthase inhibitors. Under the CAZy classification system, fungi and plant members fall in the glycosyltransferase 48 family (GT48). Some members of the glycosyltransferase 2 family (Pfam ), such as the curdlan synthase CrdS (), also has a similar activity.


1,3-Beta-glucan synthase
The biosynthesis of disaccharides, oligosaccharides, and polysaccharides involves the action of hundreds of different glycosyltransferases. These enzymes catalyse the transfer of sugar moieties from activated donor molecules to specific acceptor molecules, forming glycosidic bonds.


1,3-Beta-glucan synthase
The family consists of various 1,3-beta-glucan synthase components including Gls1, Gls2, and Gls3 from yeast. 1,3-Beta-glucan synthase (EC ) also known as callose synthase catalyses the formation of a beta-1,3-glucan polymer that is a major component of the fungal cell wall. The reaction catalysed is:


1,3-Bis(dicyanomethylene)squarate
1,3-Bis(dicyanomethylene)squarate is a divalent anion with chemical formula C10N4O2−2 or ((N≡C−)2C=)2(C4O2)2−. It is one of the pseudo-oxocarbon anions, as it can be described as a derivative of the squarate oxocarbon anion C4O2−4 through the replacement of two opposite oxygen atoms by dicyanomethylene groups =C(−C≡N)2.


1,3-Bis(dicyanomethylene)squarate
The anion can be obtained by reacting squaric acid with aniline to form the diester 1,3-dianiline squarate (a yellow solid), before treating the diester with malononitrile (N≡C−)2CH2 and sodium ethoxide to give the disodium tetrahydrate salt 2Na+·C10N4O2−2·4H2O, an orange water-soluble solid. The hydrated salt loses the water below 100 °C, but the resulting anhydrous salt is stable up to 400 °C. Reaction of the sodium salt with salts of other cations in ethanol affords the following salts:


1,3-Bis(dicyanomethylene)squarate
Nuclear magnetic resonance shows that the aromatic character of the squarate core is retained.


1,3-Bis(diphenylphosphino)propane
1,3-Bis(diphenylphosphino)propane (dppp) is an organophosphorus compound with the formula Ph2P(CH2)3PPh2. The compound is a white solid that is soluble in organic solvents. It is slightly air-sensitive, degrading in air to the phosphine oxide. It is classified as a diphosphine ligand in coordination chemistry and homogeneous catalysis.


1,3-Bis(diphenylphosphino)propane
The diphosphine can be prepared by the reaction of lithium diphenylphosphide and 1,3-dichloropropane (Ph = C6H5):


1,3-Bis(diphenylphosphino)propane
However, it can be synthesised via a much more controllable (and cheaper) route, via metal-halogen exchange and then metathesis:


1,3-Bis(diphenylphosphino)propane, Coordination chemistry and use as co-catalyst
The diphosphine serves as a bidentate ligand forming six-membered C3P2M chelate ring with a natural bite angle of 91°. For example, the complex dichloro(1,3-bis(diphenylphosphino)propane)nickel is prepared by combining equimolar portions of the ligand and nickel(II) chloride hexahydrate. This nickel complex serves as a catalyst for the Kumada coupling reaction. Dppp is also used as a ligand for palladium(II) catalysts to co-polymerize carbon monoxide and ethylene to give polyketones. Dppp can sometimes be used in palladium-catalyzed arylation under Heck reaction conditions to control regioselectivity.


1,3-Bisphosphoglyceric acid
1,3-Bisphosphoglyceric acid (1,3-Bisphosphoglycerate or 1,3BPG) is a 3-carbon organic molecule present in most, if not all, living organisms. It primarily exists as a metabolic intermediate in both glycolysis during respiration and the Calvin cycle during photosynthesis. 1,3BPG is a transitional stage between glycerate 3-phosphate and glyceraldehyde 3-phosphate during the fixation/reduction of CO2. 1,3BPG is also a precursor to 2,3-bisphosphoglycerate which in turn is a reaction intermediate in the glycolytic pathway.


1,3-Bisphosphoglyceric acid, Biological structure and role
1,3-Bisphosphoglycerate is the conjugate base of 1,3-bisphosphoglyceric acid. It is phosphorylated at the number 1 and 3 carbons. The result of this phosphorylation gives 1,3BPG important biological properties such as the ability to phosphorylate ADP to form the energy storage molecule ATP.


1,3-Bisphosphoglyceric acid, Biological structure and role, In glycolysis
Compound  at KEGG Pathway Database. Enzyme  at KEGG Pathway Database. Compound  at KEGG Pathway Database. Enzyme  at KEGG Pathway Database. Compound  at KEGG Pathway Database.


1,3-Bisphosphoglyceric acid, Biological structure and role, In glycolysis
As previously mentioned 1,3BPG is a metabolic intermediate in the glycolytic pathway. It is created by the exergonic oxidation of the aldehyde in G3P. The result of this oxidation is the conversion of the aldehyde group into a carboxylic acid group which drives the formation of an acyl phosphate bond. This is incidentally the only step in the glycolytic pathway in which NAD+ is converted into NADH. The formation reaction of 1,3BPG requires the presence of an enzyme called glyceraldehyde-3-phosphate dehydrogenase.


1,3-Bisphosphoglyceric acid, Biological structure and role, In glycolysis
The high-energy acyl phosphate bond of 1,3BPG is important in respiration as it assists in the formation of ATP. The molecule of ATP created during the following reaction is the first molecule produced during respiration. The reaction occurs as follows;


1,3-Bisphosphoglyceric acid, Biological structure and role, In glycolysis
The transfer of an inorganic phosphate from the carboxyl group on 1,3BPG to ADP to form ATP is reversible due to a low ΔG. This is as a result of one acyl phosphate bond being cleaved whilst another is created. This reaction is not naturally spontaneous and requires the presence of a catalyst. This role is performed by the enzyme phosphoglycerate kinase. During the reaction phosphoglycerate kinase undergoes a substrate induced conformational change similar to another metabolic enzyme called hexokinase.


1,3-Bisphosphoglyceric acid, Biological structure and role, In glycolysis
Because two molecules of glyceraldehyde-3-phosphate are formed during glycolysis from one molecule of glucose, 1,3BPG can be said to responsible for two of the ten molecules of ATP produced during the entire process. Glycolysis also uses two molecules of ATP in its initial stages as a committed and irreversible step. For this reason glycolysis is not reversible and has a net produce of 2 molecules of ATP and two of NADH. The two molecules of NADH themselves go on to produce approximately 3 molecules of ATP each.


1,3-Bisphosphoglyceric acid, Biological structure and role, In glycolysis
Click on genes, proteins and metabolites below to link to respective articles.


1,3-Bisphosphoglyceric acid, Biological structure and role, In the Calvin cycle
1,3-BPG has a very similar role in the Calvin cycle to its role in the glycolytic pathway. For this reason both reactions are said to be analogous. However the reaction pathway is effectively reversed. The only other major difference between the two reactions is that NADPH is used as an electron donor in the calvin cycle whilst NAD+ is used as an electron acceptor in glycolysis. In this reaction cycle 1,3BPG originates from 3-phosphoglycerate and is made into glyceraldehyde 3-phosphate by the action of specific enzymes.


1,3-Bisphosphoglyceric acid, Biological structure and role, In the Calvin cycle
Contrary to the similar reactions of the glycolytic pathway, 1,3BPG in the Calvin cycle does not produce ATP but instead uses it. For this reason it can be considered to be an irreversible and committed step in the cycle. The outcome of this section of the cycle is an inorganic phosphate is removed from 1,3BPG as a hydrogen ion and two electrons are added to the compound+.


1,3-Bisphosphoglyceric acid, Biological structure and role, In the Calvin cycle
In complete reverse of the glycolytic pathway reaction, the enzyme phosphoglycerate kinase catalyses the reduction of the carboxyl group of 1,3BPG to form an aldehyde instead. This reaction also releases an inorganic phosphate molecule which is subsequently used as energy for the donation of electrons from the conversion of NADPH to NADP+. Overseeing this latter stage of the reaction is the enzyme glyceraldehyde-phosphate dehydrogenase.


1,3-Bisphosphoglyceric acid, Biological structure and role, In oxygen transfer
During normal metabolism in humans approximately 20% of the 1,3BPG produced does not go any further in the glycolytic pathway. It is instead shunted through an alternate pathway involving the reduction of ATP in the erythrocytes. During this alternate pathway it is made into a similar molecule called 2,3-bisphosphoglyceric acid (2,3BPG). 2,3BPG is used as a mechanism to oversee the efficient release of oxygen from hemoglobin. Levels of this 1,3BPG will raise in a patients blood when oxygen levels are low as this is one of the mechanisms of acclimatization. Low oxygen levels trigger a rise in 1,3BPG levels which in turn raises the level of 2,3BPG which alters the efficiency of oxygen dissociation from hemoglobin.


1,3-Butanediol
1,3-Butanediol is an organic compound with the formula CH3CH(OH)CH2CH2OH. With two alcohol functional groups, the molecule is classified as a diol. The compound is a colorless, water-soluble liquid. It is one of four common structural isomers of butanediol. It has no large scale uses.


1,3-Butanediol, Occurrence
In biology, 1,3-butanediol is used as a hypoglycaemic agent. 1,3-Butanediol can be converted into β-hydroxybutyrate and serve as a substrate for brain metabolism.


1,3-Cycloheptadiene
1,3-Cycloheptadiene is a highly flammable cycloalkene that occurs as a colorless clear liquid.


1,3-Cyclohexanedione
1,3-Cyclohexanedione is an organic compound with the formula (CH2)4(CO)2. It is one of three isomeric cyclohexanediones. It is a colorless compound that occurs naturally. It is the substrate for cyclohexanedione hydrolase. The compound exists mainly as the enol tautomer.


1,3-Cyclohexanedione, Synthesis, structure, and reactivity
1,3-Cyclohexanedione exists in solution as the enol. It reacts under acid catalysis with alcohols to 3-alkoxyenones.


1,3-Cyclohexanedione, Synthesis, structure, and reactivity
Its pKa is 5.26. Treatment of the sodium salt of the enolate with methyl iodide gives 2-methyl-1,3-cyclohexanedione, which despite the name, also exists predominantly as the enol.


1,3-Cyclohexanedione, Derivatives
Several herbicides against grasses are formal derivatives of 1,3-cyclohexanedione. Examples of commercial products include cycloxydim, clethodim, tralkoxydim, butroxydim, profoxydim, and mesotrione.


1,3-Cyclopentanedione
1,3-Cyclopentanedione is an organic compound with the formula (CH2)3(CO)2. It is one of two isomeric cyclopentanediones, the other being 1,2-cyclopentanedione. The enol is predicted to be about 1-3 kcal/mol more stable than the diketo form. The enol structure has been confirmed by X-ray crystallography.


1,3-Cyclopentanedione, Preparation
The compound is prepared by hydrogenation of 2-cyclopentene-1,4-dione using zinc/acetic acid.


1,3-Dehydroadamantane
1,3-Dehydroadamantane, formally tetracyclo[3.3.1.13,7.01,3]decane, is an organic compound with formula C10H14, which can be obtained from adamantane by removal of two hydrogen atoms to create an internal bond. It is a polycyclic hydrocarbon, and can be viewed also as being derived from [3.3.1]propellane by addition of a methylene bridge between the two larger rings.


1,3-Dehydroadamantane
Like other small-ring propellanes, this compound is substantially strained and unstable.


1,3-Dehydroadamantane, Synthesis
1,3-Dehydroadamantane was obtained in 1969 by Richard Pincock and Edward Torupka, by reduction of 1,3-dibromoadamantane according to the scheme below:


1,3-Dehydroadamantane, Reactions, Oxidation
On standing in solution, it reacts with oxygen from air (with a half-life of 6 hours), yielding a peroxide. The latter converts to a dihydroxide by reaction with lithium aluminium hydride.


1,3-Dehydroadamantane, Reactions, Polymerization
Like [1.1.1]propellane, 1,3-dehydroadamantane can be polymerized by breaking the axial bond and joining the resulting radicals into a linear chain:


1,3-Dehydroadamantane, Reactions, Polymerization
In this scheme, 1,3-dehydroadamantane is reacted with acrylonitrile in a radical polymerization initiated with lithium metal in tetrahydrofuran. The resulting alternating copolymer has a glass transition temperature of 217 °C


1,3-Diaminopropane
1,3-Diaminopropane, also known as trimethylenediamine, is a simple diamine with the formula H2N(CH2)3NH2. A colourless liquid with a fishy odor, it is soluble in water and many polar organic solvents. It is isomeric with 1,2-diaminopropane. Both are building blocks in the synthesis of heterocycles, such as those used in textile finishing, and coordination complexes. It is prepared by the amination of acrylonitrile followed by hydrogenation of the resulting aminopropionitrile.


1,3-Diaminopropane
The potassium salt was used in the alkyne zipper reaction.


1,3-Diaminopropane
Known uses of 1,3-diaminopropane are in the synthesis of piroxantrone and losoxantrone.


1,3-Diaminopropane, Safety
1,3-Diaminopropane is toxic on skin exposure with an LD50 of 177 mg kg−1 (dermal, rabbit)


1,3-Diazepine
1,3-Diazepine is a diazepine. It is a scaffold found in some natural products and drugs. It is found in the drugs pentostatin and avibactam. Coformycin is a naturally occurring antibiotic.


1,3-Dibromopropane
1,3-Dibromopropane is an organobromine compound with the formula (CH2)3Br2. It is a colorless liquid with sweet odor. It is used in organic synthesis to form C3-bridged compounds such as through C-N coupling reactions.


1,3-Dibromopropane
1,3-Dibromopropane was used in the first cyclopropane synthesis in 1881, known as the Freund reaction.


1,3-Dibromopropane, Synthesis
1,3-Dibromopropane can be prepared via the free radical addition between allyl bromide and hydrogen bromide.


1,3-Dibromopropane, Metabolism
Metabolism of 1,3-dibromopropane was examined in 1981. The examination was done by orally administering 1,3-dibromopropane to rats and collecting results 24 hours after administration. Results were obtained from three sources: urine, faeces, and expired air. Upon analysis of the urinary results, researchers discovered the formation of metabolite, N-acetyl-S-(1-bromo-3-propyl)-cysteine and the decline in the GSH content of the liver of the rats. This led to the assumption that 1,3-dibromopropane could have reacted with GSH after administration and gave rise to 1-bromo-3-propyl-S-glutathione, which ultimately form the urinary metabolite. Moreover, due to little radioactivity observed from feces and the confirmation from maintained blood levels of radioactivity proved the occurrence of biliary excretion of sulfur-containing metabolites and enterohepatic cycling.


1,3-Dichloro-2-nitrobenzene
1,3-Dichloro-2-nitrobenzene is an organic compound with the formula C6H3Cl2(NO2). It is one of several isomeric dichloronitrobenzenes. It is an off-white solid that is soluble in conventional organic solvents.


1,3-Dichloro-2-nitrobenzene
The compound can be prepared by oxidation of 2,6-dichloroaniline using peroxytrifluoroacetic acid.


1,3-Dichlorobenzene
1,3-Dichlorobenzene is an organic compound with the formula C6H4Cl2. It is the least common of the three isomers of dichlorobenzene, it is a colorless liquid that is insoluble in water. It is produced as a minor byproduct of the chlorination of benzene, but can also be prepared in a directed manner by the Sandmeyer reaction of 3-chloroaniline. It also arises from the isomerization of the other dichlorobenzenes at high temperature.


1,3-Dichlorobenzene, Hazards
This chemical is combustible. "Hazardous decomposition products" are carbon monoxide, carbon dioxide, chlorine, hydrogen chloride gas. It is toxic to aquatic life with long-lasting effects.


1,3-Dichloropropan-2-ol
1,3-Dichloropropan-2-ol (1,3-DCP) is an organic compound with the formula HOCH2CHClCH2Cl. It is a colorless liquid. It is an intermediate in the production of epichlorohydrin.


1,3-Dichloropropan-2-ol
1,3-DCP is a believed to be a carcinogen and mutagen. The International Agency for Research on Cancer classifies it as a Group 2B carcinogen ("possibly carcinogenic to humans").


1,3-Dichloropropan-2-ol
Along with 3-monochloropropane-1,2-diol (3-MCPD), 1,3-DCP is found in some Asian style sauces such as soy sauce and oyster sauce.


1,3-Dichloropropane
1,3-Dichloropropane is a compound of chlorine, hydrogen, and carbon. It may  be found as a contaminant in soil fumigants containing 1,3-dichloropropene. It has low acute toxicity.


1,3-Dichloropropene
1,3-Dichloropropene, sold under diverse trade names,  is an organochlorine compound. It is colorless liquid with a sweet smell. It dissolves in water and evaporates easily. It is used mainly in farming as a pesticide, specifically  as a preplant fumigant and nematicide. It is widely used in the US and other countries, but is in the process of being phased out in the European Union.


1,3-Dichloropropene, Production, chemical properties, biodegradation
It is a byproduct in the chlorination of propene to make allyl chloride.


1,3-Dichloropropene, Production, chemical properties, biodegradation
It is usually obtained as a mixture of the geometric isomers, called Z-1,3-dichloropropene, and E-1,3-dichloropropene. Although it was first applied in agriculture in the 1950s, at least two biodegradation pathways have evolved. One pathway degrades the chlorocarbon to acetaldehyde via chloroacrylic acid.


1,3-Dichloropropene, Safety
The TLV-TWA for 1,3-dichloropropene (DCP) is 1 ppm. It is a contact irritant. A wide range of complications have been reported.


1,3-Dichloropropene, Safety, Carcinogenicity
Evidence for the carcinogenicity of 1,3-dichloropropene in humans is inadequate, but results from several cancer bioassays provide adequate evidence of carcinogenicity in animals. In the US, the Department of Health and Human Services (DHHS) has determined that 1,3-dichloropropene may reasonably be anticipated to be a carcinogen. The International Agency for Research on Cancer (IARC) has determined that 1,3-dichloropropene is possibly carcinogenic to humans. The EPA has classified 1,3-dichloropropene as a probable human carcinogen.


1,3-Dichloropropene, Use
1,3-Dichloropropene is used as a pesticide in the following crops:


1,3-Dichloropropene, Market history
Under the brand name Telone, 1,3-D was one of Dow AgroSciences's products until the merger into DowDuPont. Then it was spun off with Corteva, and as of 2020 has been licensed to Telos Ag Solutions and is no longer a Corteva product.


1,3-Difluoro-2-propanol
1,3-Difluoro-2-propanol is a metabolic poison which disrupts the citric acid cycle and is used as a rodenticide, similar to sodium fluoroacetate. It is the main ingredient (along with 1-chloro-3-fluoro-2-propanol) in the rodenticide product Gliftor which was widely used in the former USSR and still approved in China.


1,3-Difluoro-trisulfane-1,1-difluoride
1,3-Difluoro-trisulfane-1,1-difluoride is an inorganic molecular substance with the structure SF3SSF, consisting of sulfur in a low oxidation state with fluorine. The compound consists of a chain of three sulfur atoms, with three fluorine atoms bonded to the sulfur on one end and the fourth fluorine bonded to the sulfur on the other end. It has a melting point of -62 °C and a boiling point of 94 °C. As a gas, it is unstable and breaks up to form SSF2 and SF4.


1,3-Difluoro-trisulfane-1,1-difluoride
SF3SSF is produced by the condensation of sulfur difluoride and an isomer of SSF2. The reaction S3F4 ⇌ SSF2 + SF2 uses 6 kJ/mol.


1,3-Difluoro-trisulfane-1,1-difluoride
Possible isomers of its S3F4 molecular formula include FSSF2SF, which has a spontaneous fluorine migration to yield F2SSSF2, which in turn spontaneously fragments to give SF2 and SSF2.


1,3-Dihydroxyanthraquinone
1,3-Dihydroxyanthraquinone, also called purpuroxanthin or xanthopurpurin, is an organic compound with formula C14H8O4 that occurs in the plant Rubia cordifolia (Indian madder). It is one of ten dihydroxyanthraquinone isomers. Its molecular structure can be viewed as being derived from anthraquinone by replacement of two hydrogen atoms (H) by hydroxyl groups (-OH).


1,3-Dihydroxyanthraquinone
Xanthopurpurin occurs in small amounts (as a glycoside) in the root of the common madder plant, Rubia tinctorum, together with alizarin, purpurin and other anthraquinone derivatives.


1,3-Dihydroxyanthraquinone, Properties
Xanthopurpurin is insoluble in hexane but soluble in chloroform. It can be obtained from solutions in the latter as reddish crystals that melt at 270–273 °C.


1,3-Dihydroxyanthraquinone, Properties
Like many dihydroxy- and trihydroxyanthraquinones, it has a purgative action, although only 1/6  as effective as 1,2,7-trihidroxyanthraquinone (anthrapurpurin).


1,3-Diisocyanatobenzene
1,3-Diisocyanatobenzene is an aromatic isocyanate with the chemical formula C8H4N2O2.


1,3-Diisopropylbenzene
1,3-Diisopropylbenzene is the aromatic hydrocarbon with the formula C6H4(CHMe2)2 (Me = CH3). It is one of three isomeric diisopropylbenzenes. This colorless liquid is prepared by thermal isomerization of 1,4-diisopropylbenzene. It is the principal industrial precursor to resorcinol via the Hock rearrangement.


1,3-Dimethyl-2-imidazolidinone
1,3-Dimethyl-2-imidazolidinone (DMI) is a cyclic urea used as a high-boiling polar aprotic solvent. It is colourless, highly polar solvent has high thermal and chemical stability. It is a homolog of the related solvent DMPU. It can be prepared from 1,2-dimethylethylenediamine by reaction with phosgene.


1,3-Dimethyl-2-imidazolidinone, Solvent
DMI has excellent solvating ability for both inorganic and organic compounds. In many applications, DMI (as well as DMPU) can be used as a substitute or replacement for the carcinogenic solvent HMPA.


1,3-Dimethyl-2-imidazolidinone, Solvent
DMI is used in a variety of applications including detergents, dyestuffs, electronic materials and in the manufacture of polymers.


1,3-Dimethylbutylamine
1,3-Dimethylbutylamine (1,3-DMBA, dimethylbutylamine, DMBA, 4-amino-2-methylpentane, or AMP), is a stimulant drug structurally related to methylhexanamine where a butyl group replaces the pentyl group. The compound is an aliphatic amine.