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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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C Locht et al.
Proceedings of the National Academy of Sciences of the United States of America, 86(9), 3075-3079 (1989-05-01)
The enzymatic ADP-ribosyltransferase activity associated with the S1 subunit of pertussis toxin is considered to be responsible for its biological effects. Although pertussis toxin has no significant homology to other ADP-ribosylating toxins such as diphtheria toxin and Pseudomonas aeruginosa exotoxin
Arunas Silanskas et al.
Biochemistry, 50(14), 2800-2807 (2011-03-18)
Regulation of proteins by light is a new and promising strategy for the external control of biological processes. In this study, we demonstrate the ability to regulate the catalytic activity of the MunI and PvuII restriction endonucleases with light. We
M Sabés et al.
Journal of biochemical and biophysical methods, 17(1), 17-24 (1988-09-01)
The use of 2-hydroxy-5-nitrobenzyl bromide for the modification of tryptophan residues in integral membrane proteins is exemplified by its application to bacteriorhodopsin from Halobacterium halobium. Complete elimination of the unreacted reagent requires delipidation of the sample with detergents and posterior
Hee Seung Kim et al.
Electrophoresis, 23(6), 956-963 (2002-03-29)
A technique based on affinity capillary electrophoresis (ACE) and chemically modified proteins was used to screen the binding sites of various drugs on human serum albumin (HSA). This involved using HSA as a buffer additive, following the site-selective modification of
A Baracca et al.
The International journal of biochemistry, 25(9), 1269-1275 (1993-09-01)
1. The F1-ATPase from bovine heart mitochondria was shown to chemically react and to absorb 2-hydroxy-5-nitrobenzyl bromide (HNB) with changes in catalytic properties. 2. The treatment of the enzyme with HNB at concentrations below 0.5 mM resulted in an increase
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