24347-58-8

Basic information

• Product Name: (R,R)-2,3-Butanediol
• Synonyms: levo-2,3-Butanediol;(2R,3R)-(-)-2,3-Butanediol, 98+%, ee:99+%;(-)-D-threo-2,3-Butylene glycol;(2R,3R)-(-)-2,3-Butanediol,98+%,99+% ee;(2R,3R)-(-)-2,3-Butanediol, 99+% ee, 98+%;(2R,3R)-(-)-2,3-Butanediol, 99+% ee, 98+% 1GR;(R,R)-(-)-2,3-Butylene Glycol (R,R)-(-)-2,3-Dihydroxybutane;(R,R)-(-)-2,3-BUTANEDIOL FOR SYNTHESIS
• CAS NO: 24347-58-8
• Molecular Formula: C₄H₁₀O₂
• Molecular Weight: 90.12
• EINECS: 246-186-9
• Product Categories: Polyols;Chiral Compounds;Diols;Analytical Chemistry;Chiral Building Blocks;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral Compound;Chiral Building Blocks;Organic Building Blocks
• Mol File: 24347-58-8.mol
• Article Data: 33

Chemical Properties

• Melting Point: 16 °C
• Boiling Point: 77.3-77.4 °C10 mm Hg(lit.)
• Flash Point: 185 °F
• Appearance: Clear colorless/Liquid
• Density: 0.992 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.26mmHg at 25°C
• Refractive Index: n20/D 1.433
• Storage Temp.: −20°C
• PKA: 14.67±0.20(Predicted)
• Water Solubility: soluble
• Sensitive: Hygroscopic
• Stability: Stable. Hygroscopic, air sensitive. Incompatible with strong oxidizing agents, acid anhydrides, acid chlorides, chloroformates,
• Merck: 14,1568
• BRN: 4290593
• CAS DataBase Reference: (R,R)-2,3-Butanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-2,3-Butanediol(24347-58-8)
• EPA Substance Registry System: (R,R)-2,3-Butanediol(24347-58-8)

Safety Data

• Hazard Codes: Xi
• Statements: 24/25:
• Safety Statements: 24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 24347-58-8(Hazardous Substances Data)

Usage

Description

(R,R)-2,3-Butanediol, also known as (2R,3R)-(-)-2,3-Butanediol, is a key building block in the pharmaceutical industry. It is a C2 symmetric chiral diol with versatile applications as a chiral auxiliary, building block, and chiral ligand. (R,R)-2,3-Butanediol is a colorless or slightly brown liquid and is defined as the (R,R) diastereoisomer of butane-2,3-diol.

Uses

Used in Pharmaceutical Industry:
(R,R)-2,3-Butanediol is used as a key building block for the synthesis of various pharmaceutical compounds due to its chiral nature and versatility.
Used in Chiral Auxiliary Applications:
(R,R)-2,3-Butanediol is employed as a chiral auxiliary in organic synthesis, aiding in the creation of chiral centers in target molecules.
Used in Chiral Ligand Applications:
It serves as a chiral ligand in asymmetric catalysis, enhancing the selectivity and efficiency of chemical reactions.
Used in Building Block Applications:
(R,R)-2,3-Butanediol is used as a building block for the synthesis of complex organic molecules, particularly in the pharmaceutical and chemical industries.
Used in Analytical Chemistry:
(R,R)-2,3-Butanediol is used in the cyclocondensation with ketones for 13C NMR determination of optical purity, which is crucial for assessing the enantiomeric composition of chiral compounds.
Used in Gas Chromatography:
It is utilized in the resolution of carbonyl compounds in gas chromatography, a technique used to separate and analyze complex mixtures of volatile compounds.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3/t3-,4?/m1/s1

Upstream product

• 58-86-6 D-xylose 
• 69-65-8 mannitol 
• 50-99-7 glucose 
• 513-86-0 3-hydroxy-2-butanon 
• 431-03-8 dimethylglyoxal 
• 925669-95-0 2,3-cis-epoxybutane 
• 57-50-1 Sucrose 
• 492-61-5 β-D-glucose 
• 930-47-2 cis-(4S,5S)-dimethyl-1,3-dioxolane 
• 147-71-7 D-tartaric acid 
• 83759-48-2 C₁₁H₁₆O₂ 
• 83759-48-2 C₁₁H₁₆O₂ 
• 6982-25-8 d,l-2,3-butanediol 
• 4437-70-1 (+/-)-trans-4,5-dimethyl-1,3-dioxolan-2-one 

Downstream Products

• 6565-31-7 (4'R,5'R)-2-(4',5'-dimethyldioxolan-2'-yl)furan 
• 18789-41-8 (4R)-2,4r,5t-trimethyl-[1,3,2]dioxaphospholane-2-oxide 
• 930-47-2 trans-4,5-Dimethyl-1,3-dioxolan 
• 61732-91-0 (R)-2-((Ξ)-1-ethyl-pentyl)-4r,5t-dimethyl-[1,3]dioxolane 
• 15479-05-7 1-Chlor-trans-4,5-dimethyl-1,3,2-dioxa-phospholan 
• 513-86-0 3-hydroxy-2-butanon 
• 6412-85-7 ((R)-2,4r,5t-trimethyl-[1,3]dioxolan-2-yl)-acetic acid ethyl ester 
• 75281-80-0 4,5-dimethyl-2-phenyl-(2α,4α,5β)-1,3-dioxolane 
• 141434-77-7 (4R,5R)-2-phenyl-2,4,5-trimethyl-1,3-dioxolane 
• 90846-70-1 D_g-threo-2-acetoxy-3-(toluene-4-sulfonyloxy)-butane 
• 64896-27-1 -2,3-butandiol di-(4-methylbenzolsulfonat) 
• 73346-75-5 (R)-2,2,4r,5t-tetramethyl-[1,3]dioxolane 
• 74839-83-1 (2S,3S)-bis(4-methylbenzenesulfonyl)butane 
• 144405-26-5 (4R,5R)-2-methoxycarbonyl-4,5-dimethyl-2-phenyl-1,3-dioxolane 

Relevant articles and documents

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Asymmetric hydroboration of [E]- and [Z]-2-methoxy-2-butenes. Synthesis of (-)-[2R,3R]-butane-2,3-diol in >97% ee

Asymmetric hydroboration of [E]- and [Z]-2-methoxy-2-butene, using (-)-diisopinocampheylborane at -25°C in THF solvent, followed by oxidation using H2O2/NaOH, gave (-)-[2R,3R]- and (+)-[2R,3S]-3-methoxy-2-butanols in >97 and 90% ee,

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.

Highly efficient and recyclable chiral Pt nanoparticle catalyst for enantioselective hydrogenation of activated ketones

Thermoregulated phase-separable chiral Pt nanoparticle catalyst exhibited excellent ee (>99%) in the enantioselective hydrogenation of activated ketones for preparing chiral α-hydroxy acetals and chiral 1,2-diols. More importantly, the chiral catalyst could be easily separated by phase separation and directly reused in the next cycle without any loss in catalytic activity and enantioselectivity, even in the gram-scale reaction. The leaching of Pt was under the detection limit of the instrument.