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107794

Sigma-Aldrich

2-Nitrobenzyl bromide

98%

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Synonym(s):
α-Bromo-2-nitrotoluene
Linear Formula:
O2NC6H4CH2Br
CAS Number:
Molecular Weight:
216.03
Beilstein/REAXYS Number:
638991
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

assay

98%

form

solid

mp

44-46 °C (lit.)

SMILES string

[O-][N+](=O)c1ccccc1CBr

InChI

1S/C7H6BrNO2/c8-5-6-3-1-2-4-7(6)9(10)11/h1-4H,5H2

InChI key

HXBMIQJOSHZCFX-UHFFFAOYSA-N

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1 of 4

This Item
N13054264458B58806
2-Nitrobenzyl bromide 98%

107794

2-Nitrobenzyl bromide

4-Nitrobenzyl bromide 99%

N13054

4-Nitrobenzyl bromide

3,4-Difluorobenzyl bromide 98%

264458

3,4-Difluorobenzyl bromide

2-Bromobenzotrifluoride 99%

B58806

2-Bromobenzotrifluoride

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

mp

44-46 °C (lit.)

mp

96-99 °C (lit.)

mp

-

mp

-

form

solid

form

solid

form

liquid

form

liquid

Application

2-Nitrobenzyl bromide was used for caging unprotected cysteine-containing or thiophosphorylated peptides in aqueous solution. It can be used in the synthesis of (R)- and (S)-3-amino-3,4-dihydro-1H-quinolin-2-one.

Biochem/physiol Actions

2-Nitrobenzyl bromide reacts with L-cysteine to form S-2-nitrobenzyl-cysteine which was used for modification of ultra-low-gelling-temperature (ULGT) agarose.

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

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


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Photoreleasable molecules are important in studies of various biological phenomena, especially cell signaling. Here we report a generally applicable approach for 'caging' unprotected cysteine-containing or thiophosphorylated peptides in aqueous solution with 2-nitrobenzyl bromides. Photolysis of the caged peptides was achieved
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A kinetic study was carried out on the solvolysis of o-nitrobenzyl bromide (o-isomer, 1) and p-nitrobenzyl bromide (p-isomer, 3), and o-nitrobenzoyl chloride (o-isomer, 2) in a wide range of solvents under various temperatures. In all of the solvents without aqueous
A practical synthesis of (R)-and (S)-3-amino-3, 4-dihydro-1H-quinolin-2-one.
Hulin B and Lopaze MG.
Tetrahedron Asymmetry, 15(12), 1957-1958 (2004)

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