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237639

Sigma-Aldrich

(2R,3R)-(−)-2,3-Butanediol

97%

Synonym(s):

(2R,3R)-2,3-butanediol, (2R,3R)-butane-2,3-diol, (R,R)-2,3-butanediol, (R,R)-2,3-butylene glycol, (R,R)-butane-2,3-diol, D-(-)-2,3-Butanediol

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About This Item

Linear Formula:
CH3CH(OH)CH(OH)CH3
CAS Number:
24347-58-8
Molecular Weight:
90.12
Beilstein:
1718901
EC Number:
246-186-9
MDL number:
MFCD00064267
UNSPSC Code:
12352001
PubChem Substance ID:
24854259
NACRES:
NA.22

Assay

97%

form

liquid

optical activity

[α]23/D −13.2°, neat

optical purity

ee: 99% (GLC)

refractive index

n20/D 1.433 (lit.)

bp

77.3-77.4 °C/10 mmHg (lit.)

density

0.987 g/mL at 25 °C (lit.)

SMILES string

C[C@@H](O)[C@@H](C)O

InChI

1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3/t3-,4-/m1/s1

InChI key

OWBTYPJTUOEWEK-QWWZWVQMSA-N

Related Categories

General description

(2R,3R)-(-)-2,3-Butanediol is a key building block in pharmaceutical industry.

Application

C2 symmetric chiral diol with versatile applications as a chiral auxiliary, building block, and chiral ligand. Cyclocondenses with ketones for 13C NMR determination of optical purity.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

185.0 °F - closed cup

Flash Point(C)

85 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tetrahedron Asymmetry, 17, 993-993 (2006)
Synlett, 275-275 (1993)
Raman optical activity of tartaric acid and related molecules.
Barron LD.
Tetrahedron, 34(5), 607-610 (1978)
Yuanzhi He et al.
Molecules (Basel, Switzerland), 23(3) (2018-03-23)
(3S)-Acetoin and (2S,3S)-2,3-butanediol are important platform chemicals widely applied in the asymmetric synthesis of valuable chiral chemicals. However, their production by fermentative methods is difficult to perform. This study aimed to develop a whole-cell biocatalysis strategy for the production of
Stolle, A. et al.
Tetrahedron Letters, 35, 3521-3521 (1994)
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