Phenylacetone

Phenylacetone

Skeletal formula
Ball-and-stick model
Names
IUPAC name 1-Phenylpropan-2-one
Other names Benzyl methyl ketone; Methyl benzyl ketone; Phenyl-2-propanone
Identifiers
CAS Number	103-79-7 Y
ChEBI	CHEBI:52052 Y
ChemSpider	21106366 Y
Jmol 3D model	Interactive image
KEGG	C15512 Y
PubChem	7678
UNII	O7IZH10V9Y Y
InChI InChI=1S/C9H10O/c1-8(10)7-9-5-3-2-4-6-9/h2-6H,7H2,1H3 Y Key: QCCDLTOVEPVEJK-UHFFFAOYSA-N Y InChI=1/C9H10O/c1-8(10)7-9-5-3-2-4-6-9/h2-6H,7H2,1H3 Key: QCCDLTOVEPVEJK-UHFFFAOYAG
SMILES O=C(C)Cc1ccccc1
Properties
Chemical 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)
Vapor pressure	{{{value}}}
Except where otherwise noted, 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. In humans, phenylacetone occurs as a metabolite of amphetamine via oxidative deamination.

Preparation

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:

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

Due to its status as a controlled substance, other laboratory scale methods have been reported. 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

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

Amphetamine metabolism

Metabolic pathways of amphetamine in humans

4-Hydroxyphenylacetone

Phenylacetone

Benzoic acid

Hippuric acid

Amphetamine

Norephedrine

4-Hydroxyamphetamine

4-Hydroxynorephedrine

Para-
Hydroxylation

Para-
Hydroxylation

Para-
Hydroxylation

Beta-
Hydroxylation

Beta-
Hydroxylation

Oxidative
Deamination

Oxidation

Glycine
Conjugation

See also

• MDP2P - related compound with a methylenedioxy group, and a precursor to MDMA.
• Cyclohexylacetone - the cyclohexane derivative of phenylacetone
• Phenylacetones
• Methamphetamine