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Sigma-Aldrich

1-Chloro-2,4-dinitrobenzene

≥99%

Synonym(s):

2,4-Dinitrochlorobenzene, CDNB, DNCB

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About This Item

Linear Formula:
ClC6H3(NO2)2
CAS Number:
97-00-7
Molecular Weight:
202.55
Beilstein:
613161
EC Number:
202-551-4
MDL number:
MFCD00007075
UNSPSC Code:
12352100
PubChem Substance ID:
24854237
NACRES:
NA.22

Quality Level

200

Assay

≥99%

form

solid

expl. lim.

22 %

bp

315 °C (lit.)

mp

48-50 °C (lit.)

solubility

alcohol: very slightly soluble (cold)(lit.)
benzene: soluble(lit.)
carbon disulfide: soluble(lit.)
diethyl ether: soluble(lit.)
water: insoluble (practically)(lit.)

functional group

chloro
nitro

SMILES string

[O-][N+](=O)c1ccc(Cl)c(c1)[N+]([O-])=O

InChI

1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H

InChI key

VYZAHLCBVHPDDF-UHFFFAOYSA-N

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General description

1-Chloro-2,4-dinitrobenzene on incubation with erythrocyte undergoes conjugation with erythrocyte glutathione (GSH) to form 2,4-dinitrophenyl-S-glutathione. It is an irreversible inhibitor of human thioredoxin reductase.

Application

1-Chloro-2,4-dinitrobenzene has been used as alkylating agent to evaluate the depletion of intracellular erythrocyte glutathione (GSH).

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 2

Flash Point(F)

381.2 °F - closed cup

Flash Point(C)

194 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL3427
BCCM1461
BCCJ4545
BCCG5072
BCCD8094

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E S Arnér et al.
The Journal of biological chemistry, 270(8), 3479-3482 (1995-02-24)
Human thioredoxin reductase is a dimeric enzyme that catalyzes reduction of the disulfide in oxidized thioredoxin by a mechanism involving transfer of electrons from NADPH via FAD to a redox-active disulfide. 1-Chloro-2,4-dinitrobenzene (DNCB) is an alkylating agent used for depleting
Y C Awasthi et al.
Blood, 58(4), 733-738 (1981-10-01)
Erythrocyte glutathione (GSH) can be rapidly depleted by incubating the cells with 1-chloro-2,4-dinitrobenzene (CDNB), which forms 2,4-dinitrophenyl-S-glutathione with GSH through the reaction catalyzed by glutathione S-transferase. GSH-CDNB conjugate thus formed stays undegraded within the erythrocytes. This indicates that in the
Cynthia M F Monaco et al.
American journal of physiology. Endocrinology and metabolism, 318(1), E44-E51 (2019-12-04)
Sexual dimorphism in mitochondrial respiratory function has been reported in young women and men without diabetes, which may have important implications for exercise. The purpose of this study was to determine if sexual dimorphism exists in skeletal muscle mitochondrial bioenergetics
M Saarnilehto et al.
Allergy, 69(10), 1424-1427 (2014-07-22)
2,4-Dinitrochlorobenzene (DNCB) is widely used in human clinical studies and in experimental animal studies to evoke allergic contact dermatitis. 2,4-Dinitrochlorobenzene is a potent immunogen capable of inducing contact sensitization in all humans exposed. However, the mechanism by which DNCB evokes
Salik Hussain et al.
Particle and fibre toxicology, 9, 15-15 (2012-05-25)
We determined the ability of a model nanoparticle (NP) (titanium dioxide, TiO(2)) to modulate sensitization induced by a known potent dermal sensitizer (dinitrochlorobenzene) using a variant of the local lymph node assay called lymph node proliferation assay.BALB/c mice received sub-cutaneous
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