2,3-butanediol 2,3-butanediol 2,3-butanediol is the organic compound with the formula (ch3choh)2. it is classified as a vic-diol (glycol). it exists as three stereoisomers, a chiral pair and the meso isomer. all are colorless liquids. applications include precursors to various plastics and pesticides. 2,3-butanediol names preferred iupac name butane-2,3-diol other names 2,3-butylene glycolpseudobutylene glycol2,3-dihydroxybutanebutan-2,3-dioldiethanol & bis-ethanol identifiers cas number 513-85-9 y19132-06-0 (2s,3s)-(+) y24347-58-8 (2r,3r)-(-) y5341-95-7 (2r,3s) y 3d model (jsmol) interactive image chebi chebi:62064 n chembl chembl2312529 chemspider 257 y echa infocard 100.007.431 ec number 208-173-6 pubchem cid 262 unii 45427zb5ij y7e9uxg71s1 (2s,3s)-(+) yor02b2286a (2r,3r)-(-) yf5ia8x9o8m (2r,3s) y comptox dashboard (epa) dtxsid8041321 inchi inchi=1s/c4h10o2/c1-3(5)4(2)6/h3-6h,1-2h3key: owbtypjtuoewek-uhfffaoysa-n smiles cc(c(c)o)o properties chemical formula c4h10o2 molar mass 90.122 g·mol−1 appearance colorless liquid odor odorless density 0.987 g/ml melting point 19 °c (66 °f; 292 k) boiling point 177 °c (351 °f; 450 k) solubility in water miscible solubility in other solvents soluble in alcohol, ketones, ether log p -0.92 vapor pressure 0.23 hpa (20 °c) acidity (pka) 14.9 refractive index (nd) 1.4366 thermochemistry heat capacity (c) 213.0 j/k mol std enthalpy offormation (δfh⦵298) -544.8 kj/mol hazards nfpa 704 (fire diamond) 1 1 0 flash point 85 °c (185 °f; 358 k) autoignitiontemperature 402 °c (756 °f; 675 k) lethal dose or concentration (ld, lc): ld50 (median dose) 5462 mg/kg (rat, oral) related compounds related butanediols 1,4-butanediol1,3-butanediol except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). n verify (what is yn ?) infobox references isomerism of the three stereoisomers, two are enantiomers (levo- and dextro-2,3-butanediol) and one is a meso compound. the enantiomeric pair have (2r, 3r) and (2s, 3s) configurations at carbons 2 and 3, while the meso compound has configuration (2r, 3s) or, equivalently, (2s, 3r). industrial production and uses 2,3-butanediol is prepared by hydrolysis of 2,3-epoxybutane: (ch3ch)2o + h2o → ch3(choh)2ch3 the isomer distribution depends on the stereochemistry of the epoxide. the meso isomer is used to combine with naphthalene-1,5-diisocyanate. the resulting polyurethane is called "vulkollan". biological production the (2r,3r)-stereoisomer of 2,3-butanediol is produced by a variety of microorganisms in a process known as butanediol fermentation. it is found naturally in cocoa butter, in the roots of ruta graveolens, sweet corn, and in rotten mussels. it is used in the resolution of carbonyl compounds in gas chromatography. during world war ii research was done towards producing 2,3-butanediol by fermentation in order to produce 1,3-butadiene, the monomer of the polybutadiene used in a leading type of synthetic rubber. it can be derived from the fermentation of sugarcane molasses. fermentative production of 2,3-butanediol from carbohydrates involves a network of biochemical reactions that can be manipulated to maximize production. 2,3-butanediol has been proposed as a rocket fuel that could be created on mars by means of cyanobacteria and e. coli, shipped from earth, working on resources available at the surface of mars. 2,3-butanediol has been detected, in peppers, grape wine, anatidaes. reactions 2,3-butanediol undergo dehydration to form butanone (methyl ethyl ketone): (ch3choh)2 → ch3c(o)ch2ch3 + h2o it can also undergo deoxydehydration to form butene: (ch3choh)2 + 2 h2 → c4h8 + 2 h2o