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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
223-558-9
Beilstein/REAXYS Number:
638991
MDL number:
Assay:
98%
Form:
solid
Quality Level
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
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.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk
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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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
Ying Luo et al.
Nature materials, 3(4), 249-253 (2004-03-23)
Tissue engineering aims to replace, repair or regenerate tissue/organ function, by delivering signalling molecules and cells on a three-dimensional (3D) biomaterials scaffold that supports cell infiltration and tissue organization. To control cell behaviour and ultimately induce structural and functional tissue
Kyoung-Ho Park et al.
International journal of molecular sciences, 20(16) (2019-08-21)
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