2,4-Dinitrochlorobenzene

2,4-Dinitrochlorobenzene

Names
Preferred IUPAC name 1-Chloro-2,4-dinitrobenzene
Other names Dinitrochlorobenzene Chlorodinitrobenzene 2,4-Dinitrochlorobenzene 2,4-Dinitrophenyl chloride 4-Chloro-1,3-dinitrobenzene
Identifiers
CAS Number	97-00-7 Y
3D model (Jmol)	Interactive image
Abbreviations	CDNB; DNCB
ChEBI	CHEBI:34718 N
ChemSpider	5 Y
ECHA InfoCard	100.002.321
EC Number	202-551-4
PubChem CID	6
InChI InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H Key: VYZAHLCBVHPDDF-UHFFFAOYSA-N
SMILES c1cc(c(cc1[N+](=O)[O-])[N+](=O)[O-])Cl
Properties
Chemical formula	C6H3ClN2O4
Molar mass	202.55 g·mol−1
Appearance	yellow crystals
Odor	almond-like
Density	1.6867 g/cm3
Melting point	54 °C (129 °F; 327 K)
Boiling point	315 °C (599 °F; 588 K)
Solubility in water	Insoluble
Solubility	soluble in ether, benzene, CS2
Refractive index (nD)	1.5857 (60 °C)
Hazards
NFPA 704	1 3 4
Explosive limits	2-22%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	1.07 g/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

2,4-Dinitrochlorobenzene (DNCB) is an organic compound with the formula (O₂N)₂C₆H₃Cl. It is a yellow solid that is soluble in organic solvents. It is an important intermediate for the industrial production of other compounds.

DNCB is produced commercially by the nitration of p-nitrochlorobenzene with a mixture of nitric and sulfuric acids. Other methods afford the compound less efficiently include the chlorination of dinitrobenzene, nitration of o-nitrochlorobenzene and the dinitration of chlorobenzene.

By virtue of the two nitro groups, the chloride is susceptible to nucleophilic substitution. In this way, the compound is a precursor to many other compounds. Base gives the dinitrophenol, ammonia the dinitroaniline, methoxide the dinitroanisole, and amines the secondary amines.

DNCB is used as a substrate in GST enzyme activity assays. The molecule is conjugated to a single molecule of reduced glutathione which then absorbs at 340 nm. Affinity of CDNB for each class of GST varies and so it is not a good measure of activity for some forms (e.g. GSTT and GSTZ).

DNCB can be used to treat warts with an effective cure rate of 80%. DNCB induces an allergic immune response toward the wart-causing virus.

DNCB induces a type IV hypersensitivity reaction in almost all people exposed to it, so it is used medically to assess the T cell activity in patients. This is a useful diagnostic test for immunocompromised patients. It can also be used to treat warts.

DNCB can cause contact dermatitis.