Propiophenone

Propiophenone
Skeletal formula of propiophenone
Ball-and-stick model of the propiophenone molecule
Names
Preferred IUPAC name
1-Phenylpropan-1-one
Other names
Ethyl phenyl ketone, BzEt
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.053 Edit this at Wikidata
UNII
  • InChI=1S/C9H10O/c1-2-9(10)8-6-4-3-5-7-8/h3-7H,2H2,1H3 checkY
    Key: KRIOVPPHQSLHCZ-UHFFFAOYSA-N checkY
  • InChI=1/C9H10O/c1-2-9(10)8-6-4-3-5-7-8/h3-7H,2H2,1H3
    Key: KRIOVPPHQSLHCZ-UHFFFAOYAT
  • CCC(=O)c1ccccc1
Properties
C9H10O
Molar mass 134.178 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
-83.73·10−6 cm3/mol
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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Propiophenone (shorthand: benzoylethane or BzEt) 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 propanoyl chloride 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

Phenmetrazine, derived from propiophenone, is an appetite suppressant.

It is an intermediate in the synthesis of the pharmaceuticals phenmetrazine and propoxyphen.[1][4][5]

Other drugs made from propiophenone include the following: PDM-35, Eprazinone, Methcathinone (leading to ephedrine), Trimebutine, Amfepramone, Diphepanol, Metamfepramone, Etoxadrol, Hydroxyphenamate, Phendimetrazine, Iminophenimide, Bencisteine, Flumecinol, Pyrroliphene, Perisone,

References

  1. ^ a b Siegel, H.; Eggersdorfer, M. "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN 978-3527306732.
  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". Organic Syntheses. 16: 44. doi:10.15227/orgsyn.016.0044.