Phenylacetone
 |
|
 |
|
| Names | |
|---|---|
| IUPAC name
1-Phenylpropan-2-one
|
|
| Other names
Benzyl methyl ketone; Methyl benzyl ketone; Phenyl-2-propanone
|
|
| Identifiers | |
103-79-7 ![Yes](data:image/svg+xml,<svg xmlns="http://www.w3.org/2000/svg" width="7" height="7"><rect fill-opacity="0"/></svg>){kind=small} |
|
| ChEBI | CHEBI:52052 |
| ChemSpider | 21106366 |
| Jmol 3D image | Interactive graph |
| KEGG | C15512 |
| PubChem | 7678 |
| UNII | O7IZH10V9Y |
| Properties | |
| 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|
 verify (what is  ?) |
|
| 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] In humans, phenylacetone occurs as a metabolite of amphetamine via oxidative deamination.
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] 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 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.
Amphetamine metabolism[edit]
See also[edit]
- MDP2P - related compound with a methylenedioxy group, and a precursor to MDMA.
- Cyclohexylacetone - the cyclohexane derivative of phenylacetone
- Phenylacetones
- Methamphetamine
References[edit]
- Jump up ^ "Lists of: Scheduling Actions, Controlled Substances, Regulated Chemicals" (PDF). U.S. Department of Justice, Drug Enforcement Administration.
- Jump up ^ Siegel, H.; Eggersdorfer, M. (2005), "Ketones", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a15_077
- Jump up ^ Synthesis of Phenyl-2-Propanone (P2P)
|
||||||||||||||||||||||||||||||||||||||
