2,4-Dinitrochlorobenzene (DNCB) is an
organic compound with the
chemical formula (O
2N)
2C
6H
3Cl. 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 The chemical element nitrogen is one of the most abundant elements in the universe and can form many compounds. It can take several oxidation states; but the most oxidation states are -3 and +3. Nitrogen can form nitride and nitrate ions. It also fo ...
and
sulfuric acid
Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
s. Other methods afford the compound less efficiently include the
chlorination of
dinitrobenzene, nitration of
o-nitrochlorobenzene and the dinitration of
chlorobenzene.
Uses
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.
Laboratory use
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).
Medical use
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.
[
]
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.
DNCB can cause contact dermatitis.
References
{{DEFAULTSORT:Dinitrochlorobenzene, 2,4-
Nitrobenzenes
Chlorobenzenes