Hexachloroacetone
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Hexachloroacetone is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula (Cl3C)2CO. 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.


Reactions and uses

Hexachloroacetone functions equivalently to
trichloroacetyl chloride Trichloroacetyl chloride is the acyl chloride of trichloroacetic acid. It can be formed by reacting chlorine with acetyl chloride Acetyl chloride (CH3COCl) is an acyl chloride derived from acetic acid. It belongs to the class of organic compo ...
, i.e. as an trichloroacetylating agent. The main use of hexachloroacetone is as a pesticide. For the use of hexachloroacetone in the preparation of a novel
insect repellent An insect repellent (also commonly called "bug spray") is a substance applied to skin, clothing, or other surfaces to discourage insects (and arthropods in general) from landing or climbing on that surface. Insect repellents help prevent and cont ...
see
Perkow reaction The Perkow reaction is an organic reaction in which a trialkyl phosphite ester reacts with a haloketone to form a dialkyl vinyl phosphate and an alkyl halide. In the related Michaelis–Arbuzov reaction the same reactants are known to form a be ...
. The industrial route to
hexafluoroacetone Hexafluoroacetone (HFA) is a chemical compound with the formula (CF3)2CO. It is structurally similar to acetone; however, its reactivity is markedly different. It a colourless, hygroscopic, nonflammable, highly reactive gas characterized by a must ...
involves treatment of hexachloroacetone with HF: :(CCl3)2CO + 6 HF → (CF3)2CO + 6 HCl


See also

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Chloroacetone Chloroacetone is a chemical compound with the formula . At STP it is a colourless liquid with a pungent odour. On exposure to light, it turns to a dark yellow-amber colour. It was used as a tear gas in World War I. Synthesis Chloroacetone may b ...
*
Dichloroacetone Bis(chloromethyl) ketone is a chemical substance with formula . It is a solid, and is used in the making of citric acid. Exposures such as contact or inhalation of bis(chloromethyl) ketone can result in irritation or damage to skin, eyes, throat ...


References

Organochlorides Ketones Pesticides {{organohalide-stub