|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||202.55 g·mol−1|
|Melting point||54 °C (129 °F; 327 K)|
|Boiling point||315 °C (599 °F; 588 K)|
|Solubility||soluble in ether, benzene, CS2|
Refractive index (nD)
|1.5857 (60 °C)|
|NFPA 704 (fire diamond)|
|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).
|what is ?)(|
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 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.