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, BzEt
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.053
UNII
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
-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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Infobox references

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[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 can also be used in the synthesis of aryl alkenes, such as phenylpropanoids.[citation needed] With a flowery odor, propiophenone is a component in some perfumes.

References[edit]

  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" [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. ; Collective Volume, 2, p. 363