5341-95-7

Basic information

• Product Name: MESO-2,3-BUTANEDIOL
• Synonyms: (R,S)-butane-2,3-diol;2,3-butanediol (meso);meso-butane-2,3-diol;MESO-2,3-BUTANEDIOL;2,3-Butanediol, (2R,3S)-rel-;meso-2,3-Butylene glycol;(2R,3S)-2,3-Butanediol;(2R,3S)-Butane-2,3-diol
• CAS NO: 5341-95-7
• Molecular Formula: C₄H₁₀O₂
• Molecular Weight: 90.12
• Product Categories: Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 5341-95-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 32-34 °C(lit.)
• Boiling Point: 183-184 °C(lit.)
• Flash Point: 185 °F
• Appearance: /
• Density: 0.99
• Vapor Pressure: 24.7-222.5Pa at 20-50℃
• Refractive Index: 1.4348
• Storage Temp.: 2-8°C
• PKA: 14.67±0.20(Predicted)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 1718900
• CAS DataBase Reference: MESO-2,3-BUTANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: MESO-2,3-BUTANEDIOL(5341-95-7)
• EPA Substance Registry System: MESO-2,3-BUTANEDIOL(5341-95-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 5341-95-7(Hazardous Substances Data)

Usage

Definition

ChEBI: The meso diastereoisomer of butane-2,3-diol.

General Description

meso-2,3-Butanediol is a diol. 2,3-Butanediol (2,3-DB) exists in three stereoisomeric forms: dextro, levo and meso. 2,3-DB is a crucial chemical feedstock and has wide applications in industry. Production of meso-2,3-butanediol under low oxygen condition by metabolically engineered Escherichia coli is reported. 2,3-Butanediol can be converted to 1,3-butadiene, which is used in the preparation of synthetic rubber. meso-2,3-Butanediol is the source of production of 2-butanol by isolates of lactic acid bacteria.

Upstream product

• 431-03-8 dimethylglyoxal 
• 513-86-0 3-hydroxy-2-butanon 

Downstream Products

• 143136-43-0 (4R,5R)-2-(Bis-ethylsulfanyl-methyl)-4,5-dimethyl-[1,3]dioxolane 
• 112853-96-0 (-)-pentamethyl-4,4',5',8,8 spirooctane-2,2'-(1,3)dioxolanne>(1S,4S,4'R,5'R,7R) 
• 112853-97-1 (-)-carbethoxy-2 pentamethyl-4,4',5',8,8 spirooctane-2',3-(1,3)dioxolanne> (1R,2S,4R,4'R,5'R,7R) 
• 83862-10-6 [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 
• 83876-18-0 [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 
• 875893-99-5 trans-2-Chloro-2-oxo-4,5-dimethyl-1,3,2-dioxaphospholane 
• 73346-75-5 (R)-2,2,4r,5t-tetramethyl-[1,3]dioxolane 
• 111955-36-3 (S)-2,2,4r,5t-tetramethyl-[1,3]dioxolane 
• 88123-07-3 2-<2-(2-hydroxy-1-methylpropoxy)ethyl>-4,5-dimethyl-1,3-dioxolane 
• 88123-07-3 2-<2-(2-hydroxy-1-methylpropoxy)ethyl>-4,5-dimethyl-1,3-dioxolane 
• 15479-05-7 2-chloro-(4R*,5R*)-dimethyl-1,3,2-dioxaphospholane 
• 90026-01-0 meso-dimethylethylene di-p-toluenesulfonate 
• 64896-27-1 -2,3-butandiol di-(4-methylbenzolsulfonat) 

Relevant articles and documents

Application of robust ketoreductase from Hansenula polymorpha for the reduction of carbonyl compounds

Enzyme-catalysed asymmetric reduction of ketones is an attractive tool for the production of chiral building blocks or precursors for the synthesis of bioactive compounds. Expression of robust ketoreductase (KRED) from Hansenula polymorpha was upscaled and applied for the asymmetric reduction of 31 prochiral carbonyl compounds (aliphatic and aromatic ketones, diketones and β-keto esters) to the corresponding optically pure hydroxy compounds. Biotransformations were performed with the purified recombinant KRED together with NADP+ recycling glucose dehydrogenase (GDH, Bacillus megaterium), both overexpressed in Escherichia coli BL21(DE3). Maximum activity of KRED for biotransformation of ethyl-2-methylacetoacetate achieved by the high cell density cultivation was 2499.7 ± 234 U g–1DCW and 8.47 ± 0.40 U·mg–1E, respectively. The KRED from Hansenula polymorpha is a very versatile enzyme with broad substrate specificity and high activity towards carbonyl substrates with various structural features. Among the 36 carbonyl substrates screened in this study, the KRED showed activity with 31, with high enantioselectivity in most cases. With several ketones, the Hansenula polymorpha KRED catalysed preferentially the formation of the (R)-secondary alcohols, which is highly valued.

Direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones

The direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones has been developed using nitrosobenzene as an oxygen source, affording α-anilinoxy-aldehydes and -ketones with excellent enantioselectivity. Reaction conditions have been optimized, and low temperature (-20 °C) was found to be a key for the successful α-aminoxylation of aldehydes, while slow addition of nitrosobenzene is essential for that of ketones. The scope of the reaction is presented.

An improved synthesis of chiral diols via the asymmetric catalytic hydrogenation of prochiral diones

The rates of the asymmetric hydrogenation of prochiral diketones catalyzed by Ru(BINAP) catalysts were substantially accelerated in the presence of small amounts of a strong acid.