Propiophenone

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
93-55-0 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:425902 YesY
ChEMBL ChEMBL193446 YesY
ChemSpider 6881 YesY
ECHA InfoCard 100.002.053
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 (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 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 can also be used in the synthesis of aryl alkenes, such as phenylpropanoids. With a flowery odor, propiophenone is a component in some perfumes.

Uses

It is an intermediate in the synthesis of pharmaceuticals and organic compounds.[6][7] It can also be used in the synthesis of aryl alkenes, such as phenylpropanoids. With a flowery odor, propiophenone is a component in some perfumes.

Propiophenone can be used in the synthesis of a variety of pharmaceutical drugs:

  1. Stimulants: PPA, ephedrine, cathinone, methcathinone, metamfepramone, amfepramone, phenmetrazine.
  2. Cathinone analogs of fenfluramine & tiflorex in EP 0007843A1 .
  3. Analgesia: dextropropoxyphene, pyrroliphene, etoxadrol,
  4. Antitussive/bronchial: diphepanol, eprazinone,
  5. Red links: oxifenamate, flumecinol, iminophenimide, and bencisteine.

Not propiophenone proper, but based on this core structure:

  1. Muscle Relaxants: Inaperisone, Tolperisone.
  2. Synthetic nonsteroidal estrogen: paroxypropione
  3. PAPP (Poison)

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" [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
  6. ↑ "propiophenone". Merriam-Webster.com. Merriam-Webster. Retrieved 2 June 2012.
  7. ↑ Hartung, Walter H.; Crossley, Frank (1936). "Isonitrosopropiophenone". Org. Synth. 16: 44. doi:10.15227/orgsyn.016.0044.; Coll. Vol., 2, p. 363
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