| Revision as of 17:04, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 456926205 of page 2,4-Dinitrochlorobenzene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 18:11, 29 November 2024 edit 2600:4040:2ca4:8700:e42d:800b:cea2:7459 (talk)No edit summary |
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{{Redirect|DNCB|the Bucharest Ring Road in Romania|Centura București}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 422080808 |
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| verifiedrevid = 477211218 |
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| ImageFile=2,4-Dinitrochlorobenzene.svg |
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| ImageFile=2,4-Dinitrochlorobenzene.svg |
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| ImageSize=130px |
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| ImageSize=130px |
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| IUPACName = 1-Chloro-2,4-dinitrobenzene |
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| ImageFile1 = 1-chloro-2,4-dinitrobenzene.JPG |
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| OtherNames = Dinitrochlorobenzene; Chlorodinitrobenzene; 2,4-Dinitrochlorobenzene; 2,4-Dinitrophenyl chloride; 4-Chloro-1,3-dinitrobenzene |
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| PIN = 1-Chloro-2,4-dinitrobenzene |
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| OtherNames = Dinitrochlorobenzene<br />Chlorodinitrobenzene<br />2,4-Dinitrochlorobenzene<br />2,4-Dinitrophenyl chloride<br />4-Chloro-1,3-dinitrobenzene |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = CDNB; DNCB |
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| Abbreviations = CDNB; DNCB |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 97-00-7 |
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| CASNo = 97-00-7 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = GE3IBT7BMN |
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| PubChem = 6 |
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| PubChem = 6 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 5 |
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| ChemSpiderID = 5 |
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| EINECS = 202-551-4 |
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| SMILES = c1cc(c(cc1(=O))(=O))Cl }} |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| Section2 = {{Chembox Properties |
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| ChEBI = 34718 |
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| C = 6 | H = 3 | Cl = 1 | N = 2 | O = 4 |
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| SMILES = c1cc(c(cc1(=O))(=O))Cl |
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| InChI = 1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H |
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| InChIKey = VYZAHLCBVHPDDF-UHFFFAOYSA-N |
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| C=6 | H=3 | Cl=1 | N=2 | O=4 |
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| Formula = |
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| Appearance = yellow crystals |
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| Density = |
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| Odor = almond-like |
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| Density = 1.6867 g/cm<sup>3</sup> |
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| BoilingPt = |
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| MeltingPtC = 54 |
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| Solubility = }} |
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| BoilingPtC = 315 |
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| Solubility = Insoluble<ref>{{cite web|title=1-Chloro-2,4-dinitrobenzene|url=http://www.sigmaaldrich.com/catalog/product/aldrich/138630?lang=en®ion=US|website=Sigma-Aldrich|access-date=8 September 2014}}</ref> |
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| Section3 = {{Chembox Hazards |
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| SolubleOther = soluble in ], ], ] |
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| RefractIndex = 1.5857 (60 °C) |
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|Section4={{Chembox Hazards |
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| ExploLimits = 2–22% |
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| NFPA-H = 3 | NFPA-F = 1 | NFPA-R = 4 |
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| LD50 = 1.07 g/kg (rat, oral) |
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'''2,4-Dinitrochlorobenzene''' ('''DNCB''') is an ] with the ] (O<sub>2</sub>N)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>Cl. It is a yellow solid that is ] in ]. It is an important intermediate for the industrial production of other compounds.<ref name=Booth>{{cite encyclopedia|author=Gerald Booth|title=Nitro Compounds, Aromatic|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2007|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a17_411|isbn=978-3527306732}}</ref> |
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DNCB is produced commercially by the ] of ] with a mixture of ] and ]s. Other methods afford the compound less efficiently include the ] of ], nitration of ] and the dinitration of ].<ref>{{cite web|title=Synthesis of 1-chloro-2,4-dinitrobenzene - F. Ullmann, Verlag S. Hirzel Leipzig, 1908 |url=https://organic-btc-ilmenau.jimdo.com/app/download/8980039020/1-Chlor-2%2C4-dinitrobenzol.pdf |access-date=19 May 2020 }}</ref> |
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==Uses== |
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By virtue of the two ]s, the chloride is susceptible to ]. In this way, the compound is a precursor to many other compounds.<ref>{{cite journal |author=J. F. Bunnett, R. M. Conner|doi=10.15227/orgsyn.040.0034|title=2,4-Dinitroiodobenzene |journal=Organic Syntheses |year=1960 |volume=40 |page=34 }}</ref><ref>{{cite journal |doi=10.15227/orgsyn.015.0022|title=2,4-Dinitroaniline |author=F. B. Wells, C. F. H. Allen|journal=Organic Syntheses |year=1935 |volume=15 |page=22 }}</ref><ref>{{cite journal |doi=10.15227/orgsyn.044.0047|title=2,4-Dinitrobenzenesulfenyl Chloride |author=Norman Kharasch, Robert B. Langford|journal=Organic Syntheses |year=1964 |volume=44 |page=47 }}</ref> |
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===Laboratory use=== |
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DNCB is used as a substrate in GST enzyme activity assays.<ref>{{cite journal |vauthors=Habig WH, Pabst MJ, Jakoby WB | year = 1974 | title = Glutathione S-transferases. The first enzymatic step in mercapturic acid formation | journal = J Biol Chem | volume = 249 | pages = 7130–7139 | pmid = 4436300 | issue = 22| doi = 10.1016/S0021-9258(19)42083-8 | doi-access = free }}</ref> The molecule is ] to a single molecule of reduced ] 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).{{Citation needed|date=April 2010}} |
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===Medical use=== |
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DNCB can be used to treat ]s with an effective cure rate of 80%.<ref name=Harvard>{{Cite web| title = Treating Warts |url = http://www.health.harvard.edu/family-health-guide/treating-warts |work = Harvard Health Publications |date = 21 September 2011 |publisher = ]}}</ref> DNCB induces an allergic immune response toward the wart-causing virus.<ref name=Harvard/> |
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== Safety == |
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DNCB induces a ] reaction in almost all people exposed to it, so it is used medically to assess the ] activity in patients. This is a useful diagnostic test for immunocompromised patients. It can also be used to treat ].<ref>{{cite web |url=http://www.health.harvard.edu/fhg/updates/update0303d.shtml |title=Treating warts |publisher=Harvard Medical School |access-date=April 2, 2010 |archive-url=https://web.archive.org/web/20101103023520/http://www.health.harvard.edu/fhg/updates/update0303d.shtml |archive-date=2010-11-03 |url-status=dead }}</ref> |
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DNCB can cause ].<ref>{{cite journal |vauthors=White SI, Friedmann PS, Moss C, Simpson JM |title=The effect of altering area of application and dose per unit area on sensitization by DNCB |journal=Br. J. Dermatol. |volume=115 |issue=6 |pages=663–8 |year=1986 |pmid=3801307 |doi= 10.1111/j.1365-2133.1986.tb06646.x|s2cid=21476276 }}</ref> |
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==References== |
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{{reflist}} |
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{{Authority control}} |
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{{DEFAULTSORT:Dinitrochlorobenzene, 2, 4-}} |
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