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237329

Sigma-Aldrich

1-Chloro-2,4-dinitrobenzene

≥99%

Sinónimos:

2,4-Dinitrochlorobenzene, CDNB, DNCB

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About This Item

Fórmula lineal:
ClC6H3(NO2)2
Número de CAS:
97-00-7
Peso molecular:
202.55
Beilstein/REAXYS Number:
613161
EC Number:
202-551-4
MDL number:
MFCD00007075
UNSPSC Code:
12352100
PubChem Substance ID:
24854237
NACRES:
NA.22

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).

signalword

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

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

wgk_germany

WGK 2

flash_point_f

381.2 °F - closed cup

flash_point_c

194 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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
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
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