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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

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Certificates of Analysis (COA)

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

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Reed, P.E. Katzenellenbogen, J.A.
The Journal of Organic Chemistry, 56, 2624-2624 (1991)
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)
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, 44(7), 1249-1253 (1992-10-06)
Glutathione (GSH) conjugation of the separate enantiomers of five 2-bromocarboxylic acids and some of their urea derivatives by rat liver GSH transferases (GSTs) was studied. The liver cytosolic fraction conjugated all compounds, except for (R)-2-bromoisovaleric acid, with a variable degree
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