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138630

Sigma-Aldrich

1-Chloro-2,4-dinitrobenzene

97%

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:
24848362
NACRES:
NA.22

Assay

97%

form

solid

expl. lim.

22 %

bp

315 °C (lit.)

mp

48-50 °C (lit.)

solubility

alcohol: soluble (hot)
alcohol: very slightly soluble (cold)
benzene: soluble
carbon disulfide: soluble
diethyl ether: soluble
water: insoluble

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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Application

1-Chloro-2,4-dinitrobenzene was used in determination of relative amounts of individual glutathione S-transferases subunits in human tissues by reverse-phase HPLC. It was used as contact sensitizer to study the antibacterial peptides hBD-2, -3 and -4 and LL-37 induced IL-18 protein release in human keratinocytes.

Biochem/physiol Actions

2,4-dinitrochlorobenzene induces atopic dermatitis in BALB/c mice model.

Preparation Note

The product is dissolved in ethanol when used as glutathione S-transferase substrate and then added to a buffer to form a final concentration of 1mM in phosphate buffer (8 mL of 0.2 M KH2PO4 and 28 mL of 0.1 M Na2HPO4 per 100 mL of solution, adjusted to pH 6.5) and 4% (v/v) ethanol.

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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1,4-Dinitrobenzene 98%

Sigma-Aldrich

102369

1,4-Dinitrobenzene

J D Rowe et al.
The Biochemical journal, 325 ( Pt 2), 481-486 (1997-07-15)
Uncertainties about the composition and identities of glutathione S-transferases (GSTs) in human tissue have impeded studies on their biological functions. A rigorous protocol has therefore been developed to characterize the human proteins. Cytosolic GST subunits were resolved by reverse-phase HPLC
Mingli Sun et al.
Molecular medicine reports, 9(2), 689-694 (2013-12-18)
Bacillus Calmette-Guerin extract (BCGE) has been proven to be clinically effective for anaphylactic disease, infectious diseases and cancer. In this study, we investigated the effect of the intramuscular application of BCGE on 2,4-dinitrochlorobenzene (DNCB)-induced atopic dermatitis (AD). We established an
François Niyonsaba et al.
Journal of immunology (Baltimore, Md. : 1950), 175(3), 1776-1784 (2005-07-22)
In addition to its physical barrier against invading microorganisms, the skin produces antimicrobial peptides, human beta-defensins (hBDs) and cathelicidin LL-37, that participate in the innate host defense. Because IL-18 is produced by keratinocytes and involved in skin diseases in which
Antony Anet et al.
Journal of hazardous materials, 370, 42-53 (2018-09-15)
This study investigates Bisphenol A (BPA) induced oxidative stress that mediates the genotoxicity in in vivo model Drosophila melanogaster. The calculated LC50 for BPA was 12.35 μg/mL. The strains of D. melanogaster were reared in 0.1, 1.0, 2.5 and 5.0 μg/mL BPA
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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