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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[1]. 2-Nitrobenzyl chloride was used to prepare 4,4′-dinitrostillbene[2].

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[3].

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBH0283
STBF0285V
S62926V
1369136
1137464

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Sigma-Aldrich

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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
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
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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