107794
2-Nitrobenzyl bromide
98%
Synonym(s):
α-Bromo-2-nitrotoluene
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About This Item
Linear Formula:
O2NC6H4CH2Br
CAS Number:
Molecular Weight:
216.03
Beilstein:
638991
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
98%
form
solid
mp
44-46 °C (lit.)
functional group
bromo
nitro
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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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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Skin Corr. 1B
Storage Class Code
8A - Combustible corrosive hazardous materials
WGK
WGK 3
Flash Point(F)
230.0 °F - closed cup
Flash Point(C)
110 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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P Pan et al.
FEBS letters, 405(1), 81-85 (1997-03-17)
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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Nature materials, 3(4), 249-253 (2004-03-23)
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A practical synthesis of (R)-and (S)-3-amino-3, 4-dihydro-1H-quinolin-2-one.
Hulin B and Lopaze MG.
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