2,4-Dinitrochlorobenzene

"DNCB" redirects here. For the Bucharest Ring Road in Romania, see Centura București.

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

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 (JSmol)	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
UNII	GE3IBT7BMN Y
CompTox Dashboard (EPA)	DTXSID6020278
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[1]
Solubility	soluble in ether, benzene, CS2
Refractive index (nD)	1.5857 (60 °C)
Hazards
NFPA 704 (fire diamond)	3 1 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 verify (what is YN ?) Infobox references

Preparation and reactions

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 1,3-dinitrobenzene, nitration of o-nitrochlorobenzene and the dinitration of chlorobenzene.^[3]

By virtue of the two nitro substituents, the chloride in DNCB is particularly susceptible to nucleophilic substitution, at least relative to simple chlorobenzene. In this way, the compound is a precursor to many other compounds.^[4][5][6] In one example, DNCB is as a substrate in Glutathione S-Transferase, relevant to activity assays.^[7]

Safety

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.^[8]

DNCB can cause contact dermatitis.^[9]