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Merck

237329

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24854237
EC Number:
202-551-4
Beilstein/REAXYS Number:
613161
MDL number:
MFCD00007075
Assay:
≥99%
Form:
solid

Key Documents

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InChI key

VYZAHLCBVHPDDF-UHFFFAOYSA-N

InChI

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

SMILES string

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

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

Quality Level

200

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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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Poisonous substance

pdsc

Group 5: Self-reactive substances + Nitro compounds + Hazardous rank I + 1st self-reactive materials

fsl

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

237329-10G:4548173337524 + 237329-VAR: + 237329-BULK: + 237329-50G:4548173337531

jan

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG5072
BCCD8094
BCCC2721
BCBZ3828
BCBW5262

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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
Jochem W van der Veen et al.
Archives of toxicology, 87(4), 763-766 (2012-11-13)
Several in vitro DNA microarray studies have shown the importance of nuclear factor (erythroid-derived 2)-like 2 (Nrf2) in skin sensitization. Nevertheless, the exact in vivo role of the Nrf2-Keap1 pathway during the induction of skin sensitization remains unknown. To study
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
Xiaoxiao Peng et al.
The Biochemical journal, 447(1), 167-174 (2012-07-13)
Thiophosphate (SPO(3)) was recently shown to promote cysteine insertion at Sec (selenocysteine)-encoding UGA codons during selenoprotein synthesis. We reported previously that irreversible targeting by cDDP [cis-diamminedichloroplatinum(II) or cisplatin] of the Sec residue in TrxR1 (thioredoxin reductase 1) contributes to cDDP
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