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Sigma-Aldrich

1-Chlor-2,4-dinitrobenzol

≥99%

Synonym(e):

2,4-Dinitro-chlorbenzol

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About This Item

Lineare Formel:
ClC6H3(NO2)2
CAS-Nummer:
97-00-7
Molekulargewicht:
202.55
Beilstein:
613161
EG-Nummer:
202-551-4
MDL-Nummer:
MFCD00007075
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24854237
NACRES:
NA.22

Assay

≥99%

Form

solid

Expl.-Gr.

22 %

bp

315 °C (lit.)

mp (Schmelzpunkt)

48-50 °C (lit.)

Löslichkeit

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

InChIKey

VYZAHLCBVHPDDF-UHFFFAOYSA-N

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Allgemeine Beschreibung

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.

Anwendung

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

Signalwort

Danger

Gefahreneinstufungen

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

Lagerklassenschlüssel

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

WGK

WGK 2

Flammpunkt (°F)

381.2 °F - closed cup

Flammpunkt (°C)

194 °C - closed cup

Persönliche Schutzausrüstung

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

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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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