Hexachloroacetone: Difference between revisions
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Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey. |
Undid revision 1245354146 by Project Osprey (talk) |
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{{chembox |
{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 400104186 |
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| Name = Hexachloroacetone |
| Name = Hexachloroacetone |
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| ImageFile = Hexachloroacetone.png |
| ImageFile = Hexachloroacetone.png |
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| ImageFile1 = Hexachloroacetone-3D-balls.png |
| ImageFile1 = Hexachloroacetone-3D-balls.png |
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| ImageSize1 = 170px |
| ImageSize1 = 170px |
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| PIN = 1,1,1,3,3,3-Hexachloropropan-2-one |
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| OtherNames = perchloroacetone<br />HCA |
| OtherNames = perchloroacetone<br />HCA |
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| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13873693 |
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| InChI = 1/C3Cl6O/c4-2(5,6)1(10)3(7,8)9 |
| InChI = 1/C3Cl6O/c4-2(5,6)1(10)3(7,8)9 |
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| InChIKey = DOJXGHGHTWFZHK-UHFFFAOYAW |
| InChIKey = DOJXGHGHTWFZHK-UHFFFAOYAW |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C3Cl6O/c4-2(5,6)1(10)3(7,8)9 |
| StdInChI = 1S/C3Cl6O/c4-2(5,6)1(10)3(7,8)9 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DOJXGHGHTWFZHK-UHFFFAOYSA-N |
| StdInChIKey = DOJXGHGHTWFZHK-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 116-16-5 |
| CASNo = 116-16-5 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C19122 |
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| ChEBI = 82243 |
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| ChEMBL = 3182582 |
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| EINECS = 204-129-5 |
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| PubChem = 8303 |
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| RTECS = UC2100000 |
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| UNNumber = 2661 |
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| UNII = RU0LGU279Y |
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| SMILES = ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl |
| SMILES = ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl |
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}} |
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| Formula = C<sub>3</sub>Cl<sub>6</sub>O |
| Formula = C<sub>3</sub>Cl<sub>6</sub>O |
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| MolarMass = 264.75 g/mol |
| MolarMass = 264.75 g/mol |
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| Density = 1. |
| Density = 1.7434 g/cm<sup>3</sup><ref>''CRC Handbook of Chemistry and Physics'', Internet Version, CRC Press (2005)</ref> |
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| MeltingPtC = -2 |
| MeltingPtC = -2 |
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| BoilingPtC = 204 |
| BoilingPtC = 204 |
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'''Hexachloroacetone''' is an [[organic compound]] with the formula Cl<sub>3</sub>C |
'''Hexachloroacetone''' is an [[organic compound]] with the formula (Cl<sub>3</sub>C)<sub>2</sub>CO. It is also called hexachloropropanone or perchloroacetone. Numbers indicating the position of the chlorine-atoms are generally omitted as all the possible positions are substituted with chlorine. It is a colorless liquid, slightly soluble in water. |
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==Reactions and uses== |
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The main use of hexachloroacetone is as a pesticide. For the use of hexachloroacetone in the preparation of a novel [[insect repellent]] see [[Perkow reaction]]. |
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Hexachloroacetone functions equivalently to [[trichloroacetyl chloride]], i.e. as an trichloroacetylating agent.<ref>{{cite journal |doi=10.15227/orgsyn.040.0103|author=Bernard Sukornick|title=α,α,α-Trichloroacetanilide|journal=Organic Syntheses|year=1960|volume=40|page=103}}</ref> |
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The main use of hexachloroacetone is as a pesticide. For the use of hexachloroacetone in the preparation of a novel [[insect repellent]] see [[Perkow reaction]]. The industrial route to [[hexafluoroacetone]] involves treatment of hexachloroacetone with HF:<ref name=Ullmanns>{{cite encyclopedia|author=Günter Siegemund |author2=Werner Schwertfeger |author3=Andrew Feiring |author4=Bruce Smart |author5=Fred Behr |author6=Herward Vogel |author7=Blaine McKusick |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|place=Weinheim|year=2002|doi=10.1002/14356007.a11_349|chapter=Fluorine Compounds, Organic|isbn=3-527-30673-0}}</ref> |
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:(CCl<sub>3</sub>)<sub>2</sub>CO + 6 HF → (CF<sub>3</sub>)<sub>2</sub>CO + 6 HCl |
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==See also== |
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* [[Chloroacetone]] |
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* [[Dichloroacetone]] |
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==References== |
==References== |
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