Phenylacetone

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Phenylacetone
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 103-79-7 YesY
PubChem 7678
ChemSpider 21106366 YesY
UNII O7IZH10V9Y YesY
KEGG C15512 YesY
ChEBI CHEBI:52052 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H10O
Molar mass 134.18 g mol−1
Appearance Colorless, pleasant odor
Density 1.006 g/mL
Melting point −15 °C (5 °F; 258 K)
Boiling point 214 to 216 °C (417 to 421 °F; 487 to 489 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Phenylacetone is an organic compound with the chemical formula C6H5CH2C(O)CH3. It is a colorless oil that is soluble in organic solvents. This substance is used in the manufacture of methamphetamine and amphetamine, where it is commonly known as P2P. Due to the illicit uses in clandestine chemistry, it was declared a schedule II controlled substance in the United States in 1980.[1] Phenylacetone is the deamination product of amphetamine metabolism in the human body.

Preparation[edit]

It is prepared commercially by ketonization of phenylacetic acid and acetic acid over alumina at 400-500 °C. The aluminum oxide serves as a catalyst for the dehydration and decarboxylation:[2]

C6H5CH2CO2H + CH3CO2H → C6H5CH2C(O)CH3 + CO2 + H2O

Due to its status as a controlled substance, other laboratory scale methods have been reported.[3][unreliable source?] It can be produced by the condensation of benzaldehyde with nitroethane, which yields phenyl-2-nitropropene followed by reduction, usually in the presence of acid, to phenylacetone.

Phenylacetone via phenyl-2-nitropropene

A conceptually simple example of phenylacetone organic synthesis is the Friedel-Crafts alkylation of benzene with chloroacetone.

Phenylacetone synthesis via the Friedel-Crafts alkylation of benzene with chloroacetone.

This is, however, typically not used due to overalkylation commonly associated with Friedel-Crafts alkylation.

Applications[edit]

Phenyl acetone is used as an intermediate in the production of pesticides and anticoagulants.

See also[edit]

References[edit]