Propiophenone
Skeletal formula of propiophenone | |
Ball-and-stick model of the propiophenone molecule | |
Names | |
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IUPAC name
1-Phenylpropan-1-one
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Other names
Ethyl phenyl ketone
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Identifiers | |
93-55-0 | |
ChEBI | CHEBI:425902 |
ChEMBL | ChEMBL193446 |
ChemSpider | 6881 |
Jmol 3D model | Interactive image |
PubChem | 7148 |
UNII | E599A8OKQH |
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Properties | |
C9H10O | |
Molar mass | 134.18 g·mol−1 |
Appearance | Colorless liquid |
Density | 1.0087 g/mL |
Melting point | 18.6 °C (65.5 °F; 291.8 K) |
Boiling point | 218 °C (424 °F; 491 K) |
Insoluble | |
Vapor pressure | {{{value}}} |
Related compounds | |
Related ketones
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Acetophenone Butyrophenone |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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verify (what is ?) | |
Infobox references | |
Propiophenone is an aryl ketone. It is a colorless, sweet-smelling liquid that is insoluble in water, but miscible with organic solvents. It is used in the preparation of other compounds.
Production
Propiophenone can be prepared by Friedel-Crafts reaction of propionic acid and benzene. It is also prepared commercially by ketonization of benzoic acid and propionic acid over calcium acetate and alumina at 450—550 °C:[1]
- C6H5CO2H + CH3CH2CO2H → C6H5C(O)CH2CH3 + CO2 + H2O
Ludwig Claisen discovered that α-Methoxystyrene forms this compound when heated for an hour at 300°C (65% yield).[2][3]
Uses
It is an intermediate in the synthesis of pharmaceuticals and organic compounds.[4][5] It is used in the synthesis of ephedrine and propiophenone derivatives such as cathinone, and methcathinone. It can also be used in the synthesis of aryl alkenes, such as phenylpropanoids. Propiophenone is a precursor also to the commercial compounds dextropropoxyphene and phenmetrazine.[1] Another propiophenone derivative used as a drug is paroxypropione.
With a flowery odor, propiophenone is a component in some perfumes.
References
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