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163481

Sigma-Aldrich

2-Methoxy-5-nitrobenzyl bromide

97%

Synonym(s):

2-Bromomethyl-4-nitroanisole, Koshland’s Reagent II

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About This Item

Linear Formula:
CH3OC6H3(NO2)CH2Br
CAS Number:
3913-23-3
Molecular Weight:
246.06
Beilstein/REAXYS Number:
1878596
EC Number:
223-471-6
MDL number:
MFCD00007329
UNSPSC Code:
12352100
PubChem Substance ID:
24849750

assay

97%

mp

76-78 °C (lit.)

SMILES string

COc1ccc(cc1CBr)[N+]([O-])=O

InChI

1S/C8H8BrNO3/c1-13-8-3-2-7(10(11)12)4-6(8)5-9/h2-4H,5H2,1H3

InChI key

JRHMPHMGOGMNDU-UHFFFAOYSA-N

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General description

2-Methoxy-5-nitrobenzyl bromide is a potential mechanism-based inactivator of enzymes that perform O-dealkylations[1].

Application

2-Methoxy-5-nitrobenzyl bromide was used to modify tryptophan residues of mouse interferon to enhance their activity[2]. It was also used as reagent for sulfhydryl modification[3].

Biochem/physiol Actions

2-Methoxy-5-nitrobenzyl bromide inactivates cytochrome P-450 in male rat liver microsomes[1].

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKBT8976V
03411DJ
12927HE
09916LC
19221CA

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M Rusckowski et al.
Journal of interferon research, 2(2), 177-185 (1982-01-01)
Mouse interferon (MuIFN) preparations containing both the alpha and beta species were treated with chemical modifying reagents specific for lysine, cysteine and tryptophan residues. The purpose was to ascertain whether reagents which modify specific amino acid residues distinguished MuIFN-alpha from
A P Armstrong et al.
Drug metabolism and disposition: the biological fate of chemicals, 27(6), 741-745 (1999-05-29)
Mechanism-based inactivators serve as probes of enzyme mechanism, function, and structure. Koshland's Reagent II (2-methoxy-5-nitrobenzyl bromide, KR-II) is a potential mechanism-based inactivator of enzymes that perform O-dealkylations. The major phenobarbital-inducible form of cytochrome P-450 in male rat liver microsomes, CYP2B1
Aldrichimica Acta, 18, 78-78 (1985)
[Comparison of auc values for caffeine and its metabolites after single and repeated administration of 2-methoxy-5-nitrobenzyl bromide].
Jakub Bojakowski et al.
Roczniki Panstwowego Zakladu Higieny, 54 Suppl, 56-56 (2003-07-30)
I V Kosarev et al.
Biochimica et biophysica acta, 790(2), 125-131 (1984-10-23)
The effect of the chemical modification of lysine, histidine, arginine, tyrosine, tryptophan residues and carboxylic groups on the cryoproperties of monoclonal human cryoglobulin M has been studied. The modification of 35-40 lysine residues and that of 42-45 arginine residues in

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