| Revision as of 21:24, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'KEGG').← Previous edit |
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{{chembox |
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{{chembox |
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| verifiedrevid = 414062085 |
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| verifiedrevid = 460029538 |
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|Reference=<ref> at ]</ref> |
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| Reference =<ref> at ]</ref> |
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|ImageFile=2,3,5,6-tetrachloro-parabenzoquinone.svg |
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| ImageFile =Chloranil structure.png |
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|ImageSize=120px |
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| ImageSize =120px |
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|IUPACName=2,3,5,6-Tetrachlorocyclohexa-2,5-diene-1,4-dione |
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| IUPACName =2,3,5,6-Tetrachlorocyclohexa-2,5-diene-1,4-dione |
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|OtherNames=Tetrachloro-''p''-benzoquinone |
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| OtherNames = ''p''-Chloranil; Tetrachloro-1,4-benzoquinone; Tetrachloro-''p''-benzoquinone |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8068 |
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| ChemSpiderID = 8068 |
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| InChI = 1/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11 |
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| InChI = 1/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11 |
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| StdInChIKey = UGNWTBMOAKPKBL-UHFFFAOYSA-N |
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| StdInChIKey = UGNWTBMOAKPKBL-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=118-75-2 |
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| CASNo =118-75-2 |
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| PubChem=8371 |
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| PubChem =8371 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = <!-- blanked - oldvalue: C18933 --> |
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| KEGG = C18933 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 01W5X7N5XV |
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| UNII = 01W5X7N5XV |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 36703 |
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| ChEBI = 36703 |
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| EC_number = 204-274-4 |
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| RTECS = DK6825000 |
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| SMILES = ClC=1C(=O)C(\Cl)=C(\Cl)C(=O)C=1Cl |
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| SMILES = ClC=1C(=O)C(\Cl)=C(\Cl)C(=O)C=1Cl |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6|Cl=4|O=2 |
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| Formula=C<sub>6</sub>Cl<sub>4</sub>O<sub>2</sub> |
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| Appearance = Yellow solid |
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| MolarMass=245.88 g/mol |
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| Density = |
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| Appearance= |
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| MeltingPtC = 295 to 296 |
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| Density= |
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| MeltingPt=295-296 °C |
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| BoilingPt= |
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| MagSus = -112.6·10<sup>−6</sup> cm<sup>3</sup>/mol |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| FlashPt= |
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| AutoignitionPt = |
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| Autoignition= |
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| RPhrases = {{R36/38}} {{R50/53}} |
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| GHSPictograms = {{GHS07}}{{GHS09}} |
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| GHSSignalWord = Warning |
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| SPhrases = {{S37}} {{S60}} {{S61}} |
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| HPhrases = {{H-phrases|315|319|410}} |
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| PPhrases = {{P-phrases|264|273|280|302+352|305+351+338|321|332+313|337+313|362|391|501}} |
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'''Chloranil''' is a ] with the molecular formula C<sub>6</sub>Cl<sub>4</sub>O<sub>2</sub>. Also known as tetrachloro-1,4-benzoquinone, it is a yellow solid. Like the parent benzoquinone, chloranil is a planar molecule<ref name=Kochi> J.-M. Lü, S. V. Rosokha, I. S. Neretin and J. K. Kochi, "Quinones as Electron Acceptors. X-Ray Structures, Spectral (EPR, UV-vis) Characteristics and Electron-Transfer Reactivities of Their Reduced Anion Radicals as Separated vs Contact Ion Pairs" Journal of the American Chemical Society 2006 128, 16708-16719.{{doi|10.1021/ja066471o}}</ref> that functions as a mild oxidant. |
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'''Chloranil''' is a ] with the molecular formula C<sub>6</sub>Cl<sub>4</sub>O<sub>2</sub>. |
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==Synthesis and use as reagent== |
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Chloranil is produced by chlorination of phenol to give ] ("hexachlorophenol"). Hydrolysis of the dichloromethylene group in this dienone gives chloranil:<ref>François Muller and Liliane Caillard "Chlorophenols" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2011. {{doi|10.1002/14356007.a07_001.pub2}}</ref> |
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:C<sub>6</sub>H<sub>5</sub>OH + 6 Cl<sub>2</sub> → C<sub>6</sub>Cl<sub>6</sub>O + 6 HCl |
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:C<sub>6</sub>Cl<sub>6</sub>O + H<sub>2</sub>O → C<sub>6</sub>Cl<sub>4</sub>O<sub>2</sub> + 2 HCl |
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Chloroanil serves as a hydrogen acceptor. It is more electrophilic than quinone itself. It is used for the aromatization reactions, such as the conversion of ]s to the benzene derivatives.<ref>Derek R. Buckle "Chloranil" in ''Encyclopedia of Reagents for Organic Synthesis'', 2001, John Wiley. {{doi|10.1002/047084289X.rc057}}</ref> |
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Chloranil is used to test for free secondary amines. This test is useful for checking for the presence of ] derivatives. It is also a good test for the successful deprotection of a secondary amine. Secondary amines react with chloranil to give a brown/red/orange derivative, the colour depending on the amine. In these reactions, the amine displaces chloride from the ring of the quinone. |
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==Commercial applications== |
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It is a precursor to many dyes, such as ] and diaziquone (AZQ), a cancer chemotherapeutic agent. |
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==See also== |
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==See also== |
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* ] |
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* ] |
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* ] (DDQ) |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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==External links== |
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{{ketone-stub}} |
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* {{PPDB|1297}} |
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