meso-2,3-Butanediol

Base Information

• Chemical Name: meso-2,3-Butanediol
• CAS No.: 5341-95-7
• Molecular Formula: C₄H₁₀O₂
• Molecular Weight: 90.1222
• European Community (EC) Number: 823-920-1
• NSC Number: 2164
• UNII: F5IA8X9O8M
• DSSTox Substance ID: DTXSID301031540
• Nikkaji Number: J238.550C
• Wikidata: Q27093418
• Metabolomics Workbench ID: 147005
• Mol file: 5341-95-7.mol

Synonyms:meso-2,3-Butanediol;5341-95-7;(2r,3s)-butane-2,3-diol;(R,S)-2,3-butanediol;meso-butanediol;erythro-2,3-Butanediol;2,3-Butanediol, meso-;UNII-F5IA8X9O8M;2,3-Butanediol, erythro-;(R,S)-butane-2,3-diol;2,3-BUTANEDIOL (MESO);2,3-Butanediol, (R*,S*)-;NSC 2164;2,3-Butanediol, (2R,3S)-rel-;F5IA8X9O8M;NSC-2164;AI3-00959;meso-butane-2,3-diol;BU9;meso-butylene glycol;2, meso-;(R,S)-butylene glycol;erythro-butane-2,3-diol;meso-2,3-dihydroxybutane;meso-2,3-butylene glycol;meso-dimethyl ethyleneglycol;(2r,3s)-2,3-butanediol;(R*,S*)-BUTANEDIOL;(R*,S*)-2,3-butanediol;(R,S)-2,3-butylene glycol;meso-2,3-Butanediol, 99%;(2S,3R)-2,3-butananediol;(2RS,3SR)-2,3-butanediol;(R*,S*)-butane-2,3-diol;(2S,3R)-butanane-2,3-diol;CHEBI:75460;(2RS,3SR)-butane-2,3-diol;NSC2164;2,3-Butanediol, meso- (8CI);DTXSID301031540;(ERYTHRO-) 2,3-BUTANEDIOL;MFCD00077669;AKOS025293375;DB02418;C20657;meso-2,3-Butanediol, puriss., >=99.0% (GC);2,3-BUTYLENE GLYCOL MESO-FORM (ERYTHRO-FORM);Q27093418;2,3-BUTYLENE GLYCOL MESO-FORM (ERYTHRO-FORM) [MI]

Chemical Property of meso-2,3-Butanediol

Chemical Property:

• Vapor Pressure: 24.7-222.5Pa at 20-50℃
• Melting Point: 32-34 °C(lit.)
• Refractive Index: 1.4348
• Boiling Point: 183-184 °C(lit.)
• PKA: 14.67±0.20(Predicted)
• Flash Point: °C
• PSA: 40.46000
• Density: 0.784g/cm³
• LogP: -0.25200
• Storage Temp.: 2-8°C
• 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:

99.9% ^*data from raw suppliers

meso-2,3-Butanediol 99% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: CC(C(C)O)O
• Isomeric SMILES: C[C@H]([C@H](C)O)O

Technology Process of meso-2,3-Butanediol

There total 5 articles about meso-2,3-Butanediol 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:

3-hydroxy-2-butanon (513-86-0,52217-02-4,51555-24-9) → 2,3-dihydroxybutane (513-85-9,5341-95-7,6982-25-8,19132-06-0,24347-58-8,35007-63-7)

Guidance literature:

With hydrogen; In n-heptane; acetic acid; toluene; at 30 ℃; for 12h; under 37503.8 Torr; enantioselective reaction; Autoclave;

DOI:10.1016/j.catcom.2018.03.012

Reference yield:

3-hydroxy-2-butanon (513-86-0,52217-02-4,51555-24-9) → (2S)-2,3-butanediol (513-85-9,5341-95-7,6982-25-8,19132-06-0,24347-58-8,35007-63-7) + 2,3-dihydroxybutane (513-85-9,5341-95-7,6982-25-8,19132-06-0,24347-58-8,35007-63-7)

Guidance literature:

With 2,3,4,5,6-pentahydroxy-hexanal; Bacillus megaterium glucose dehydrogenase; recombinant Hansenula polymorpha ketoreductase; nicotinamide adenine dinucleotide; In aq. phosphate buffer; at 37 ℃; for 24h; pH=6.5; Optical yield = 66 percent ee; enantioselective reaction; Enzymatic reaction;

DOI:10.1016/j.mcat.2020.111364

upstream raw materials:

dimethylglyoxal

3-hydroxy-2-butanon

Downstream raw materials:

meso-dimethylethylene di-p-toluenesulfonate

-2,3-butandiol di-(4-methylbenzolsulfonat)

(-)-pentamethyl-4,4',5',8,8 spirooctane-2,2'-(1,3)dioxolanne>(1S,4S,4'R,5'R,7R)

(-)-carbethoxy-2 pentamethyl-4,4',5',8,8 spirooctane-2',3-(1,3)dioxolanne> (1R,2S,4R,4'R,5'R,7R)