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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.)

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

Certificates of Analysis (COA)

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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
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
R Li et al.
Allergy, 67(10), 1250-1258 (2012-08-23)
We previously reported that prior nasal administration of highly attenuated Bordetella pertussis BPZE1 provides effective and sustained protection against lethal challenge with influenza A viruses. The protective effect was mediated by suppressing the production of major pro-inflammatory mediators. To further
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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