Propiophenone

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Propiophenone
Skeletal formula of propiophenone
Ball-and-stick model of the propiophenone molecule
Names
IUPAC name
1-Phenylpropan-1-one
Other names
Ethyl phenyl ketone
Identifiers
93-55-0 YesY
ChEBI CHEBI:425902 YesY
ChEMBL ChEMBL193446 YesY
ChemSpider 6881 YesY
Jmol 3D model Interactive image
PubChem 7148
UNII E599A8OKQH YesY
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
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[edit]

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[edit]

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.

More examples include, diethylpropion (aka Amfepramone), as well as Oxifenamate (hydroxyphenamate), Flumecinol, Diphepanol and Etoxadrol.

With a flowery odor, propiophenone is a component in some perfumes.

References[edit]

  1. ^ a b 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" [On a peculiar rearrangement]. 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. ^ Hartung, Walter H.; Crossley, Frank (1936). "Isonitrosopropiophenone". Org. Synth. 16: 44. doi:10.15227/orgsyn.016.0044. ; Coll. Vol. 2, p. 363