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107336

Sigma-Aldrich

2-Nitrobenzyl chloride

99%

Synonym(s):

α-Chloro-2-nitrotoluene

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About This Item

Linear Formula:
O2NC6H4CH2Cl
CAS Number:
612-23-7
Molecular Weight:
171.58
Beilstein:
388396
EC Number:
210-300-5
MDL number:
MFCD00007185
UNSPSC Code:
12352100
PubChem Substance ID:
24846764
NACRES:
NA.22

Assay

99%

form

solid

bp

127-133 °C/10 mmHg (lit.)

mp

46-48 °C (lit.)

solubility

ethanol: soluble 98%

SMILES string

[O-][N+](=O)c1ccccc1CCl

InChI

1S/C7H6ClNO2/c8-5-6-3-1-2-4-7(6)9(10)11/h1-4H,5H2

InChI key

BXCBUWKTXLWPSB-UHFFFAOYSA-N

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Application

2-Nitrobenzyl chloride was used in the synthesis of S-(2-nitrobenzyl)cysteine which was inserted into human erythropoietin. 2-Nitrobenzyl chloride was used to prepare 4,4′-dinitrostillbene.

Biochem/physiol Actions

2-Nitrobenzyl chloride reacts with N-methyldiethanolamine and further reaction of the resulting quaternary diol with thionyl chloride at room temperature yields nitrobenzyl mustard quaternary salts.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

233.6 °F

Flash Point(C)

112 °C

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’.

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W A Denny et al.
International journal of radiation oncology, biology, physics, 29(2), 317-321 (1994-05-15)
To explore the utility of a new class of compounds, nitrobenzyl mustard quaternary salts, as hypoxia-selective prodrugs of diffusible cytotoxins. The parent compound N,N-bis(2-chloroethyl)-N-methyl-N-(2-nitrobenzyl)ammonium chloride (SN 25246) was prepared by reaction of 2-nitrobenzyl chloride with N-methyldiethanolamine, and reaction of the
Taek Jin Kang et al.
FEBS letters, 517(1-3), 211-214 (2002-06-14)
Using Escherichia coli cell-free protein synthesis system and aminoacylated amber suppressor tRNA, we successfully inserted an unnatural amino acid S-(2-nitrobenzyl)cysteine into human erythropoietin. Three different types of translation stop suppression were observed and each of the three types was easily
Influence of steric effects on the excited triplet-state lifetime of 2, 2'-dinitrostilbene and 2, 2', 4, 4', 6, 6'-hexanitrostilbene in acetonitrile solution.
Smit KJ.
The Journal of Physical Chemistry, 96(16), 6555-6558 (1992)

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