2,4-Dinitrochlorobenzene Explained

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 important intermediate for the industrial production of other compounds.[1]

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.[2]

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.[3] [4] [5]

Laboratory use

DNCB is used as a substrate in GST enzyme activity assays.[6] 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%.[7] DNCB induces an allergic immune response toward the wart-causing virus.[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]

Notes and References

  1. Encyclopedia: Gerald Booth. Nitro Compounds, Aromatic. Ullmann's Encyclopedia of Industrial Chemistry. 2007. Wiley-VCH. Weinheim. 10.1002/14356007.a17_411. 978-3527306732.
  2. Web site: Synthesis of 1-chloro-2,4-dinitrobenzene - F. Ullmann, Verlag S. Hirzel Leipzig, 1908 . 19 May 2020 .
  3. J. F. Bunnett, R. M. Conner. 10.15227/orgsyn.040.0034. 2,4-Dinitroiodobenzene . Organic Syntheses . 1960 . 40 . 34 .
  4. 10.15227/orgsyn.015.0022. 2,4-Dinitroaniline . F. B. Wells, C. F. H. Allen. Organic Syntheses . 1935 . 15 . 22 .
  5. 10.15227/orgsyn.044.0047. 2,4-Dinitrobenzenesulfenyl Chloride . Norman Kharasch, Robert B. Langford. Organic Syntheses . 1964 . 44 . 47 .
  6. Habig WH, Pabst MJ, Jakoby WB . 1974 . Glutathione S-transferases. The first enzymatic step in mercapturic acid formation . J Biol Chem . 249 . 7130–7139 . 4436300 . 22. 10.1016/S0021-9258(19)42083-8 . free .
  7. Web site: Treating Warts . Harvard Health Publications . 21 September 2011 . Harvard Medical School.
  8. Web site: Treating warts . Harvard Medical School . April 2, 2010 . https://web.archive.org/web/20101103023520/http://www.health.harvard.edu/fhg/updates/update0303d.shtml . 2010-11-03 . dead .
  9. White SI, Friedmann PS, Moss C, Simpson JM . The effect of altering area of application and dose per unit area on sensitization by DNCB . Br. J. Dermatol. . 115 . 6 . 663–8 . 1986 . 3801307 . 10.1111/j.1365-2133.1986.tb06646.x. 21476276 .

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