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237639

Sigma-Aldrich

(2R,3R)-(−)-2,3-Butanediol

97%

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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
Linear Formula:
CH3CH(OH)CH(OH)CH3
CAS Number:
Molecular Weight:
90.12
Beilstein/REAXYS Number:
1718901
EC Number:
MDL number:
PubChem Substance ID:
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

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1 of 4

This Item
B8490430034942038
vibrant-m

237639

(2R,3R)-(−)-2,3-Butanediol

vibrant-m

B84904

2,3-Butanediol

vibrant-m

300349

(2S,3S)-(+)-2,3-Butanediol

vibrant-m

42038

2,3-Butanediol

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

refractive index

n20/D 1.433 (lit.)

refractive index

n20/D 1.433 (lit.)

refractive index

n20/D 1.433 (lit.)

refractive index

n20/D 1.433 (lit.), n20/D 1.438

bp

77.3-77.4 °C/10 mmHg (lit.)

bp

183-184 °C (lit.)

bp

179-182 °C (lit.)

bp

183-184 °C (lit.)

density

0.987 g/mL at 25 °C (lit.)

density

1.002 g/mL at 20 °C (lit.)

density

0.987 g/mL at 25 °C (lit.)

density

1.002 g/mL at 20 °C (lit.)

form

liquid

form

liquid

form

liquid

form

-

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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

185.0 °F - closed cup

flash_point_c

85 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


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Barron LD.
Tetrahedron, 34(5), 607-610 (1978)
Tetrahedron Asymmetry, 17, 993-993 (2006)
Synlett, 275-275 (1993)
Journal of the American Chemical Society, 115, 4602-4602 (1993)
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

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