(2S,3S)-butane-2,3-diol

Base Information

• Chemical Name: (2S,3S)-butane-2,3-diol
• CAS No.: 19132-06-0
• Molecular Formula: C4H10O2
• Molecular Weight: 90.1222
• Hs Code.: 29053995
• European Community (EC) Number: 813-634-5
• UNII: 7E9UXG71S1
• DSSTox Substance ID: DTXSID401031117
• Nikkaji Number: J208.152K
• Wikidata: Q27102089
• Metabolomics Workbench ID: 50659
• Mol file: 19132-06-0.mol

Synonyms:19132-06-0;(2S,3S)-butane-2,3-diol;(S,S)-2,3-Butanediol;(2S,3S)-(+)-2,3-Butanediol;(S,S)-(+)-2,3-butanediol;(S,S)-Butane-2,3-diol;2,3-Butanediol, (+)-;(2s,3s)-2,3-butanediol;(+)-2,3-butanediol;(S,S)-2,3-Butylene glycol;2,3-Butanediol, (S-(R*,R*))-;UNII-7E9UXG71S1;7E9UXG71S1;MFCD00063648;2,3-Butanediol, [S-(R*,R*)]-;2,3-Butanediol #;L-(+)-2,3-Butanediol;2,3-BUTANEDIOL, L-;CHEBI:16812;(S-(R,R))-butane-2,3-diol;DTXSID401031117;(S,S)-(+)-2,3-Dihydroxybutane;L-(+)-BUTANE-2,3-DIOL;(S,S)-(+)-2,3-Butylene Glycol;AKOS015840290;2,3-BUTANEDIOL, (2S,3S)-;AC-26495;AS-57290;(2S,3S)-(+)-2,3-Butanediol, 97%;B1343;CS-0106462;2,3-BUTYLENE GLYCOL L(+)-THREO-FORM;C03046;C73651;EN300-141852;A813483;2,3-BUTYLENE GLYCOL L(+)-THREO-FORM [MI];J-012367;Q27102089;L-(+)-2,3-Butanediol, for chiral derivatization, >=97.0%

Chemical Property of (2S,3S)-butane-2,3-diol

Chemical Property:

• Appearance/Colour: Slightly yellow oily liquid
• Vapor Pressure: 0.26mmHg at 25°C
• Melting Point: 20°C
• Refractive Index: n20/D 1.433
• Boiling Point: 180.7 °C at 760 mmHg
• PKA: 14.67±0.20(Predicted)
• Flash Point: 85 °C
• PSA: 40.46000
• Density: 0.997 g/cm³
• LogP: -0.25200
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: soluble
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 90.068079557
• Heavy Atom Count: 6
• Complexity: 30.5

Purity/Quality:

98% ^*data from raw suppliers

(2S,3S)-2,3-Butanediol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 24/25:
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C(C)O)O
• Isomeric SMILES: C[C@@H]([C@H](C)O)O
• Description: 2, 3-Butanediol, which is very important for a variety of chemical feedstocks and liquid fuels, can be derived from the bioconversion of natural resources1-2. It may be used in the production of antifreeze solvents, extraction solvents, butadiene, polymers, polyurethane and diacetyl and may also be used as a fuel1, 2. It can be used as a precursor in the manufacture of a range of chemical products, various plastics and pesticides, including the solvents methyl ethyl ketone (MEK), gamma-butyrolactone (GBL), and 1, 3-butadiene3. Methyl ethyl ketone can be used as a liquid fuel additive. Many other derivatives for potential uses as antifreeze agent (levo-form of 2,3 BDL), solvents, and plastic can also be prepared from 2.3-BDL. Furthermore, it can be added as a flavoring agent in food products when converted to a diacetyl by dehydrogenation2. Nowadays, it has been more and more applied of microbial fermentation for the production of 2.3-BDL2,4.
• Uses: (S,S)-2,3-Butanediol is the (S,S)-isomer of 2,3-Butanediol (B690020), a naturally occurring compound found in cocoa butter.

Technology Process of (2S,3S)-butane-2,3-diol

There total 40 articles about (2S,3S)-butane-2,3-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

dimethylglyoxal (431-03-8) → (2S)-2,3-butanediol (513-85-9,5341-95-7,6982-25-8,19132-06-0,24347-58-8,35007-63-7)

Guidance literature:

dimethylglyoxal; With diphenylsilane; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (S,S)-2,2''-bis[(R)-1-(Et₂P)ethyl]-1,1''-biferrocene; In 1,2-dimethoxyethane; at 0 ℃; for 26h;

With methanol; potassium carbonate; In 1,2-dimethoxyethane; at 20 ℃; for 10h;

DOI:10.1246/bcsj.73.485

Reference yield: 50.0%

dimethylglyoxal (431-03-8) → (2S,3S)-butane-2,3-diol (19132-06-0) + (2R,3S)-2,3-butanediol (1029272-42-1) + (R,R)-2,3-butandiol (24347-58-8) + (S)-acetoin (78183-56-9,51555-24-9) + (R)-acetoin (53584-56-8,51555-24-9)

Guidance literature:

With hydrogen; Pt/Al₂O₃; cinchonine; In toluene; for 1.91667h; under 80256.4 Torr; Rate constant; Product distribution; different reaction times;

DOI:10.1039/a801390j

Reference yield: 50.0%

dimethylglyoxal (431-03-8) → (2S,3S)-butane-2,3-diol (19132-06-0) + (2R,3S)-2,3-butanediol (1029272-42-1) + (R,R)-2,3-butandiol (24347-58-8) + (R)-acetoin (53584-56-8,51555-24-9)

Guidance literature:

With hydrogen; Pt/Al₂O₃; cinchonine; In toluene; for 1.91667h; under 80256.4 Torr; Further byproducts given. Yields of byproduct given;

DOI:10.1039/a801390j

upstream raw materials:

D-xylose

glucose

2,3-cis-epoxybutane

Sucrose

Downstream raw materials:

(4R,5R)-2-(Bis-ethylsulfanyl-methyl)-4,5-dimethyl-[1,3]dioxolane

[3-((4R,5R)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-4,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl]-acetic acid methyl ester

[3-((4R,5R)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-4,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl]-acetic acid 2-trimethylsilanyl-ethyl ester

2-<2-(2-hydroxy-1-methylpropoxy)ethyl>-4,5-dimethyl-1,3-dioxolane

Refernces

• 1、 Bystroem, Styrbjoern,Hoegberg, Hans-Erik,Norin, Torbjoern. "CHIRAL SYNTHESIS OF (2S,3S,7S)-3,7-DIMETHYLPENTADECAN-2-YL ACETATE AND PROPIONATE, POTENTIAL SEX PHEROMONE COMPONENTS OF THE PINE SAW-FLY NEODIPRION SERTIFER (GEOFF.)". . p. 2249 - 2254. Retrieved 1981.
• 2、 Giovannini, P. Paolo,Medici, Alessandro,Bergamini, Carlo M.,Rippa, Mario. "Properties of diacetyl (acetoin) reductase from Bacillus stearothermophilus". . p. 1197 - 1201. Retrieved 1996.
• 3、 Petrovi?ová, Tatiana,Gyuranová, Dominika,Pl?, Michal,Myrtollari, Kamela,Smonou, Ioulia,Rebro?, Martin. "Application of robust ketoreductase from Hansenula polymorpha for the reduction of carbonyl compounds". . . Retrieved 2021/02/05.
• 4、 -. "MICRO-ORGANISM FOR THE PRODUCTION OF STEREO-SPECIFIC S, S-2,3-BUTANEDIOL". Page/Page column 27-28. . Retrieved 2016/07/05.