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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.)

functional group

bromo
carboxylic acid

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

Signal Word

Danger

Hazard Statements

H302 + H312 + H332,H314

Hazard Classifications

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

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

462101-BULK:
462101-25G:
462101-5G:
462101-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
MKBQ1596V
11413DH
05531EE
19729DA
10629KI

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Virgilio, A.A. et al.
Tetrahedron Letters, 37, 6961-6961 (1996)
Sierra, T. et al.
Journal of the American Chemical Society, 114, 7645-7645 (1992)
Reed, P.E. Katzenellenbogen, J.A.
The Journal of Organic Chemistry, 56, 2624-2624 (1991)
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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