Skip to Content
Merck
All Photos(1)

Documents

107794

Sigma-Aldrich

2-Nitrobenzyl bromide

98%

Synonym(s):

α-Bromo-2-nitrotoluene

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
O2NC6H4CH2Br
CAS Number:
3958-60-9
Molecular Weight:
216.03
Beilstein:
638991
EC Number:
223-558-9
MDL number:
MFCD00007184
UNSPSC Code:
12352100
PubChem Substance ID:
24846780
NACRES:
NA.22

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

Looking for similar products? Visit Product Comparison Guide

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
GHS05

Signal Word

Danger

Hazard Statements

H314

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

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

N-Methylcyclohexylamine 99%

Sigma-Aldrich

103322

N-Methylcyclohexylamine

2-Bromobenzyl bromide 98%

Sigma-Aldrich

187070

2-Bromobenzyl bromide

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
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
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
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)
Xu Yang et al.
Polymers, 12(4) (2020-04-09)
Photoresponsive polymers have attracted increasing interest for a variety of applications. Here, we report a family of photoresponsive polypeptoid-based copolymer poly(ethylene glycol)-b-poly(N-(S-(o-nitrobenzyl)-thioethyl) glycine)-co-poly(N-(2-phenylethyl) glycine) (PEG-b-PNSN-co-PNPE) synthesized by the controlled ring-opening polymerization (ROP) technique. The key feature of the design is
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service