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ChemicalBook >  Product Catalog >  Organic Chemistry >  Alcohols,Phenols,Phenol alcohols >  Acyclic alcohols >  (S,S)-2,3-Butanediol

(S,S)-2,3-Butanediol

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(S,S)-2,3-Butanediol Basic information

Product Name:
(S,S)-2,3-Butanediol
Synonyms:
  • (S-(R,R))-butane-2,3-diol
  • (2S,3S)-(+)-2,3-BUTANEDIOL
  • (2S,3S)-2,3-BUTANEDIOL
  • 2,3-BUTANEDIOL, [S-(R*,R*)]-
  • L(+)-2,3-BUTANEDIOL
  • (S,S)-(+)-2,3-DIHYDROXYBUTANE
  • (S,S)-(+)-2,3-BUTANEDIOL
  • (S,S)-2,3-BUTANEDIOL
CAS:
19132-06-0
MF:
C4H10O2
MW:
90.12
Product Categories:
  • organic alcohol
  • 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
  • Polyols
  • 19132-06-0
Mol File:
19132-06-0.mol
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(S,S)-2,3-Butanediol Chemical Properties

Melting point:
20°C
alpha 
13 º (c=neat)
Boiling point:
179-182 °C (lit.)
Density 
0.987 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.433
Flash point:
185 °F
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
pka
14.67±0.20(Predicted)
form 
Oily Liquid
color 
Slightly yellow
Specific Gravity
0.987
PH
9-10 (500g/l, H2O, 20℃)
explosive limit
3.1-11.4%(V)
optical activity
[α]20/D +13°, neat
Water Solubility 
soluble
BRN 
1718899
Stability:
hygroscopic
LogP
-0.655 (est)
CAS DataBase Reference
19132-06-0(CAS DataBase Reference)
NIST Chemistry Reference
2,3-Butanediol, [S-(R*,R*)]-(19132-06-0)
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Safety Information

Hazard Codes 
Xi
Safety Statements 
24/25
RIDADR 
NA 1993 / PGIII
WGK Germany 
3
HS Code 
29053995

MSDS

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(S,S)-2,3-Butanediol Usage And Synthesis

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.

Reference

  1. https://www.sigmaaldrich.com/catalog/product/sial/18967?lang=en&region=US
  2. Lee, Jinwon, et al. "Biological production of 2,3-butanediol." Applied Microbiology & Biotechnology 55.1(2001):10-8.
  3. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3147483/
  4. Oliver, John W. K., et al. "Cyanobacterial conversion of carbon dioxide to 2, 3-butanediol. PNAS 110.4(2013):1249-1254.

Chemical Properties

SLIGHTLY YELLOW OILY LIQUID

Uses

(S,S)-2,3-Butanediol is the (S,S)-isomer of 2,3-Butanediol (B690020), a naturally occurring compound found in cocoa butter.

Definition

ChEBI: The (S,S) diastereoisomer of butane-2,3-diol.

General Description

L-(+)-2,3-Butanediol is a stereoisomer of 2,3-Butanediol (2,3-BD). 2,3-BD may be used in the production of antifreeze solvents, extraction solvents, butadiene, polymers, polyurethane and diacetyl and may also be used as a fuel.

Purification Methods

Purify it by fractional distillation. The bis-(4-nitrobenzoate) has m 141-142o and [] (-) or (+) 52o (c 4 CHCl3). [Ghirardelli & Lucas J Am Chem Soc 79 734 1957, Rubin et al. J Am Chem Soc 74 425 1952, Neish Can J Res 27 6 1949, Neish & Ledingham Can J Res 27 694 1949, Beilstein 1 IV 2524-2525.]

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