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 images 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 noted otherwise, data is 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 heat 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]

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". 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