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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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
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
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