Phenylacetone
Phenylacetone | |
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IUPAC name 1-Phenylpropan-2-one | |
Other names Benzyl methyl ketone; Methyl benzyl ketone; Phenyl-2-propanone | |
Identifiers | |
CAS number | 103-79-7 |
PubChem | 7678 |
ChemSpider | 21106366 |
UNII | O7IZH10V9Y |
KEGG | C15512 |
ChEBI | CHEBI:52052 |
Jmol-3D images | Image 1 |
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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 |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
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 in the human body.
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:[2]
- C6H5CH2CO2H + CH3CO2H → C6H5CH2C(O)CH3 + CO2 + H2O
Due to its status as a controlled substance, other laboratory scale methods have been reported.[3] 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.
A conceptually simple example of phenylacetone organic synthesis is the Friedel-Crafts acylation of benzene with chloroacetone.
Applications
Phenyl acetone is used as an intermediate in the production of pesticides and anticoagulants.
See also
- MDP2P - related compound with a methylenedioxy group, and a precursor to MDMA.
- Cyclohexylacetone - the cyclohexane derivative of phenylacetone
- Phenylacetones
References
- ↑ Lists of: Scheduling Actions, Controlled Substances, Regulated Chemicals. U.S. Department of Justice, Drug Enforcement Administration.
- ↑ Siegel, H.; Eggersdorfer, M. (2005), "Ketones", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a15_077
- ↑ Synthesis of Phenyl-2-Propanone (P2P)