Propiophenone

Propiophenone

Names
IUPAC name 1-Phenylpropan-1-one
Other names Ethyl phenyl ketone
Identifiers
CAS Number	93-55-0
ChEBI	CHEBI:425902
ChEMBL	ChEMBL193446
ChemSpider	6881
Jmol interactive 3D	Image
PubChem	7148
UNII	E599A8OKQH
InChI InChI=1S/C9H10O/c1-2-9(10)8-6-4-3-5-7-8/h3-7H,2H2,1H3 Key: KRIOVPPHQSLHCZ-UHFFFAOYSA-N InChI=1/C9H10O/c1-2-9(10)8-6-4-3-5-7-8/h3-7H,2H2,1H3 Key: KRIOVPPHQSLHCZ-UHFFFAOYAT
SMILES CCC(=O)c1ccccc1
Properties
Chemical formula	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)
Solubility in water	Insoluble
Related compounds
Related ketones	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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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

1. Siegel, H.; Eggersdorfer, M. (2005), "Ketones", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a15_077
2. Claisen, Ludwig (1896). "Ueber eine eigenthümliche Umlagerung". Berichte der deutschen chemischen Gesellschaft 29 (3): 2931–2933. doi:10.1002/cber.189602903102.
3. Spielman, M. A.; Mortenson, C. W. (1940). "The Condensation of α-Methoxystyrene with Halogen Compounds". Journal of the American Chemical Society 62 (6): 1609–1610. doi:10.1021/ja01863a076.
4. "propiophenone". Merriam-Webster.com. Merriam-Webster. Retrieved 2 June 2012.
5. Walter H. Hartung and Frank Crossley (1943). "Isonitrosopropiophenone". Org. Synth.; Coll. Vol. 2, p. 363