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Merck
CN

468347

(R)-(+)-2-Bromo-3-methylbutyric acid

96%

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About This Item

Linear Formula:
(CH3)2CHCH(Br)CO2H
CAS Number:
76792-22-8
Molecular Weight:
181.03
NACRES:
NA.22
PubChem Substance ID:
24870509
UNSPSC Code:
12352101
MDL number:
MFCD00210113

Key Documents

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Product Name

(R)-(+)-2-Bromo-3-methylbutyric acid, 96%

InChI

1S/C5H9BrO2/c1-3(2)4(6)5(7)8/h3-4H,1-2H3,(H,7,8)/t4-/m1/s1

SMILES string

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

InChI key

UEBARDWJXBGYEJ-SCSAIBSYSA-N

assay

96%

optical activity

[α]22/D +21°, c = 37 in benzene

bp

90-100 °C/0.5 mmHg (lit.)

mp

35-40 °C (lit.)

functional group

bromo
carboxylic acid

Quality Level

200

Related Categories

Application

(R)-(+)-2-Bromo-3-methylbutyric acid can be used:
  • As an anionic counterpart of morpholinium based chiral ionic liquids applicable in the Heck arylation reaction of 2,3-dihydrofuran.
  • As a starting material in the synthesis of fructosyl peptide oxidase inhibitors.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

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

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
0000323972
0000323972
0000267544
0000267544
0000213776

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Synthesis and inhibitory activity of substrate-analog fructosyl peptide oxidase inhibitors
Watanabe B, et al.
Bioorganic & Medicinal Chemistry Letters, 25(18), 3910-3913 (2015)
Effect of chiral ionic liquids on palladium-catalyzed Heck arylation of 2, 3-dihydrofuran
Roszak R, et al.
Applied Catalysis A: General, 409, 148-155 (2011)
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
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
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

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