2,4-Dinitrochlorobenzene

DNCB the Bucharest Ring Road in Romania Centura București changed changed 477211218 2,4-Dinitrochlorobenzene.svg 130px 1-chloro-2,4-dinitrobenzene.JPG 1-Chloro-2,4-dinitrobenzene DinitrochlorobenzeneChlorodinitrobenzene2,4-Dinitrochlorobenzene2,4-Dinitrophenyl chloride4-Chloro-1,3-dinitrobenzene CDNB; DNCB correct CAS 97-00-7 correct FDA GE3IBT7BMN 6 correct chemspider 5 202-551-4 changed EBI 34718 c1cc(c(cc1[N+](=O)[O-])[N+](=O)[O-])Cl 1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H VYZAHLCBVHPDDF-UHFFFAOYSA-N 6 3 1 2 4 yellow crystals almond-like 1.6867 g/cm3 54 315 Insoluble1-Chloro-2,4-dinitrobenzene http://www.sigmaaldrich.com/catalog/product/aldrich/138630?lang=en&region=US Sigma-Aldrich 8 September 2014 soluble in ether, benzene, CS2 1.5857 (60 °C) 2–22% 3 1 4 1.07 g/kg (rat, oral) 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.Gerald Booth Nitro Compounds, Aromatic Ullmann's Encyclopedia of Industrial Chemistry 2007 Wiley-VCH Weinheim 10.1002/14356007.a17_411 978-3527306732 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.Synthesis of 1-chloro-2,4-dinitrobenzene - F. Ullmann, Verlag S. Hirzel Leipzig, 1908 https://organic-btc-ilmenau.jimdo.com/app/download/8980039020/1-Chlor-2%2C4-dinitrobenzol.pdf 19 May 2020 August 2026 InternetArchiveBot 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. For example, the chloride can be replaced by iodide easily.J. F. Bunnett, R. M. Conner 10.15227/orgsyn.040.0034 free 2,4-Dinitroiodobenzene Organic Syntheses 1960 40 34 10.15227/orgsyn.015.0022 free 2,4-Dinitroaniline F. B. Wells, C. F. H. Allen Organic Syntheses 1935 15 22 10.15227/orgsyn.044.0047 free 2,4-Dinitrobenzenesulfenyl Chloride Norman Kharasch, Robert B. Langford Organic Syntheses 1964 44 47 Reaction of DNCB with ammonia gives 2,4-dinitrochloroaniline, again a versatile precursor. DNCB is as a substrate in glutathione S-transferase, relevant to activity assays.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 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.http://www.health.harvard.edu/fhg/updates/update0303d.shtml 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 DNCB can cause contact dermatitis.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 References Category:Nitrobenzene derivatives Category:Chlorobenzene derivatives