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140112

Sigma-Aldrich

4-Nitrobenzyl chloride

99%

Synonym(s):

α-Chloro-4-nitrotoluene

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About This Item

Linear Formula:
O2NC6H4CH2Cl
CAS Number:
100-14-1
Molecular Weight:
171.58
Beilstein:
387187
EC Number:
202-822-7
MDL number:
MFCD00007374
UNSPSC Code:
12352100
PubChem Substance ID:
24848454
NACRES:
NA.22

Quality Level

100

Assay

99%

form

solid

mp

70-73 °C (lit.)

solubility

chloroform: soluble 50 mg/mL, clear to very slightly hazy, faintly yellow

functional group

chloro
nitro

SMILES string

[O-][N+](=O)c1ccc(CCl)cc1

InChI

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

InChI key

KGCNHWXDPDPSBV-UHFFFAOYSA-N

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General description

4-Nitrobenzyl chloride acts as substrate for glutathione S-transferase(GST) in determination of GST in Chinese fetal liver. It undergoes reduction by NADPH to yield 4-nitrotoluene.

Application

4-Nitrobenzyl chloride was used to prepare unsymmetrically N,N′-bis(substituted) 4,13-diaza-18-crown-6-ether derivatives.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBB6109
STBB6109V
S42416V
S42416-019
02330JJ

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P Jemth et al.
The Journal of biological chemistry, 275(12), 8618-8624 (2000-03-18)
Ser(11) in rat glutathione transferase T2-2 is important for stabilization of the reactive enzyme-bound glutathione thiolate in the reaction with 1-menaphthyl sulfate. The S11A mutation increased the pK(a) value for the pH dependence of the rate constant for pre-steady-state product
Tetrahedron Letters, 34, 95-95 (1993)
S B Lei et al.
Zhongguo yao li xue bao = Acta pharmacologica Sinica, 11(5), 389-391 (1990-09-01)
Subcellular fractions were isolated from Chinese fetal liver at 4-8 months of age for the determination of glutathione S-transferase (GST). Using 1-chloro-2,4-dinitrobenzene (CDNB) as substrate, GST activity was found to be 66 +/- 34 nmol/(min.mg protein), mainly in the cytosol.
Shingo Arakawa et al.
Drug metabolism and disposition: the biological fate of chemicals, 40(3), 497-503 (2011-12-16)
We investigated the impact of glutathione transferases Mu 1 (GSTM1)- and glutathione transferase Theta 1 (GSTT1)-null genotypes on hepatic GST activities in humans and compared the results with those of Gstm1- and Gstt1-null mice. In liver with GSTM1/Gstm1-null genotype, GST
P Jemth et al.
Biochemistry, 38(31), 9982-9991 (1999-08-06)
The reaction mechanism of rat glutathione transferase T2-2 has been studied using pre-steady-state and steady-state kinetics. Several parts of the catalytic cycle including binding of substrates, product formation, and product release were investigated. Under saturating conditions, a two-step product release
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