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162906

Sigma-Aldrich

2-Hydroxy-5-nitrobenzyl bromide

90%

Synonym(s):

α-Bromo-4-nitro-o-cresol, 2-Bromomethyl-4-nitrophenol, Koshland I, Koshland’s Reagent I

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About This Item

Linear Formula:
HOC6H3(NO2)CH2Br
CAS Number:
772-33-8
Molecular Weight:
232.03
Beilstein:
1868798
EC Number:
212-248-9
MDL number:
MFCD00007340
UNSPSC Code:
12352100
PubChem Substance ID:
24850013
NACRES:
NA.22

Assay

90%

form

solid

mp

144-149 °C (lit.)

solubility

chloroform: soluble 25 mg/mL, clear, yellow

functional group

bromo
nitro

storage temp.

2-8°C

SMILES string

Oc1ccc(cc1CBr)[N+]([O-])=O

InChI

1S/C7H6BrNO3/c8-4-5-3-6(9(11)12)1-2-7(5)10/h1-3,10H,4H2

InChI key

KFDPCYZHENQOBV-UHFFFAOYSA-N

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General description

2-Hydroxy-5-nitrobenzyl bromide is a protein modifying reagent.

Application

2-Hydroxy-5-nitrobenzyl bromide was used in covalent modification of tryptophan and tryptophan residues in monoclonal immunoglobulin. It was also used as reagent for sulfhydryl modification

Other Notes

Contains 2-hydroxy-5-nitrobenzyl alcohol

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000140474
0000140474
MKBG5488V
09508DD
16426CR

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A I Korneliuk et al.
Bioorganicheskaia khimiia, 11(5), 605-612 (1985-05-01)
The structural accessibility of tryptophan residues in leucyl-tRNA synthetase from cow mammary gland has been studied using chemical modifications by N-bromosuccinimide and 2-hydroxy-5-nitrobenzyl bromide. The modifications were monitored by UV absorbance and intrinsic fluorescence of the enzyme's tryptophan residues. Under
A Baracca et al.
Biochemistry international, 21(6), 1135-1142 (1990-09-01)
The incubation of bovine mitochondrial F1-ATPase with 2-hydroxy-5-nitrobenzyl bromide (HNB), a selective reagent toward tryptophan residues in proteins, produced a concentration dependent inactivation of the enzyme and the covalent binding of 0.88 mol reagent/mol F1. Although HNB is highly specific
G Solaini et al.
The Biochemical journal, 327 ( Pt 2), 443-448 (1997-11-14)
Treatment of bovine heart submitochondrial particles with a low concentration of 2-hydroxy-5-nitrobenzyl bromide (HNB), a selective reagent for the Trp residue of the epsilon subunit [Baracca, Barogi, Lenaz and Solaini (1993) Int. J. Biochem. 25, 1269-1275], enhances the ATP hydrolytic
S S Keskar et al.
The Biochemical journal, 261(1), 49-55 (1989-07-01)
Extracellular xylanase produced in submerged culture by a thermotolerant Streptomyces T7 growing at 37-50 degrees C was purified to homogeneity by chromatography on DEAE-cellulose and gel filtration on Sephadex G-50. The purified enzyme has an Mr of 20,463 and a
V A Lapuk et al.
Biokhimiia (Moscow, Russia), 50(2), 237-242 (1985-02-01)
The modification of tryptophan residues in monoclonal immunoglobulin M (IgM) by 2-hydroxy-5-nitrobenzyl bromide (RK) was studied at pH 2.0-2.85 and 7.0 and a RK to tryptophan molar ratio (K) from 1 to 40. At pH 2.85, the number of RK
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