2,4-Dinitrochlorobenzene

2,4-Dinitrochlorobenzene
IUPAC name

1-Chloro-2,4-dinitrobenzene
Other names

Dinitrochlorobenzene; Chlorodinitrobenzene; 2,4-Dinitrochlorobenzene; 2,4-Dinitrophenyl chloride; 4-Chloro-1,3-dinitrobenzene
Identifiers
Abbreviations CDNB; DNCB
CAS number 97-00-7 Y
PubChem 6
ChemSpider 5 Y
Jmol-3D images Image 1
Properties
Molecular formula C6H3ClN2O4
Molar mass 202.55 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2,4-Dinitrochlorobenzene (DNCB) is a benzene derivative. It is an electrophilic, cytotoxic compound that is used in biochemical research involving glutathione-S-transferases (GSTs).

Uses

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.[1]

DNCB is used as a substrate in GST enzyme activity assays.[2] The molecule is conjugated to a single molecule of reduced glutathione which then fluoresces 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).

Safety

DNCB can cause contact dermatitis.[3]

References

  1. ^ "Treating warts". Harvard Medical School. http://www.health.harvard.edu/fhg/updates/update0303d.shtml. Retrieved April 2, 2010. 
  2. ^ Habig WH, Pabst MJ, Jakoby WB (1974). "Glutathione S-transferases. The first enzymatic step in mercapturic acid formation". J Biol Chem 249 (22): 7130–7139. PMID 4436300. 
  3. ^ White SI, Friedmann PS, Moss C, Simpson JM (1986). "The effect of altering area of application and dose per unit area on sensitization by DNCB". Br. J. Dermatol. 115 (6): 663–8. doi:10.1111/j.1365-2133.1986.tb06646.x. PMID 3801307.