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462101

Sigma-Aldrich

(S)-(−)-2-Bromo-3-methylbutyric acid

96%

Synonym(s):

(S)-2-Bromoisovaleric acid

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About This Item

Linear Formula:
(CH3)2CHCH(Br)CO2H
CAS Number:
26782-75-2
Molecular Weight:
181.03
MDL number:
MFCD00210114
UNSPSC Code:
12352101
PubChem Substance ID:
24869940

assay

96%

form

solid

optical activity

[α]22/D −21°, c = 37 in benzene

bp

90-100 °C/0.5 mmHg (lit.)

mp

39-44 °C (lit.)

SMILES string

CC(C)[C@H](Br)C(O)=O

InChI

1S/C5H9BrO2/c1-3(2)4(6)5(7)8/h3-4H,1-2H3,(H,7,8)/t4-/m0/s1

InChI key

UEBARDWJXBGYEJ-BYPYZUCNSA-N

Application

Ferroelectric liquid crystal derivatives, proline-valine pseudo dipeptides which are potent inhibitors of α-chymotrypsin, and β-turn peptidomimetics have been prepared using this bromoacid.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKBQ1596V
11413DH
05531EE
20909JO
20823MO

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Virgilio, A.A. et al.
Tetrahedron Letters, 37, 6961-6961 (1996)
Reed, P.E. Katzenellenbogen, J.A.
The Journal of Organic Chemistry, 56, 2624-2624 (1991)
Sierra, T. et al.
Journal of the American Chemical Society, 114, 7645-7645 (1992)
J M Te Koppele et al.
The Biochemical journal, 252(1), 137-142 (1988-05-15)
The stereoselectivity of purified rat GSH transferases towards alpha-bromoisovaleric acid (BI) and its amide derivative alpha-bromoisovalerylurea (BIU) was investigated. GSH transferase 2-2 was the only enzyme to catalyse the conjugation of BI and was selective for the (S)-enantiomer. The conjugation
M Polhuijs et al.
Biochemical pharmacology, 38(22), 3957-3962 (1989-11-15)
The glutathione (GSH) conjugation of (R)-and (S)-alpha-bromoisovaleric acid (BI) in the rat in vivo, and its stereoselectivity, have been characterized. After administration of racemic [1-14C]BI two radioactive metabolites were found in bile: only one of the possible diastereomeric BI-GSH conjugates
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