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
CAS Number
  • 93-55-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:425902 checkY
ChEMBL
  • ChEMBL193446 checkY
ChemSpider
  • 6881 checkY
ECHA InfoCard 100.002.053 Edit this at Wikidata
PubChem CID
  • 7148
UNII
  • E599A8OKQH checkY
CompTox Dashboard (EPA)
  • DTXSID2044470 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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)
Solubility in water
 Insoluble
Magnetic susceptibility (χ)
 -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
Chemical compound

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

Propiophenone is used in the synthesis of a variety of pharmaceutical drugs:[1][4][5]

For example, SK&F 70463-A has a mixture of stimulant as well as depressant properties.

  1. Cathinone derivatives, e.g. Methcathinone, Metamfepramone, Amfepramone, Ethcathinone & α-PPP [19134-50-0].
  2. Ephedrine & Norephedrine.
  3. Phenmetrazine & phendimetrazine & PDM-35.
  4. Dextropropoxyphene & Pyrrolifene (sp. Pyrroliphene)
  5. Diphepanol
  6. Etoxadrol
  7. Eprazinone
  8. Hydroxyphenamate
  9. Trimebutine & Fedotozine
  10. Oxifenamate
  11. Flumecinol
  12. Iminophenimide
  13. Bencisteine
  14. Perisone
  15. CID:67948865 (Hungarian nootropic):[6]
  16. SK&F 70463-A HCl: [1477-79-8] Ref:[7] Patent:[8]
  17. R 1204 & R 960[9]
  18. alpha,alpha-Diphenyl-beta-methyl-1-pyrrolidinepropanol [2260-35-7]

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.
  6. ^ Karoly Nador, et al. WO1991008200 ().
  7. ^ Barron, D. I.; Hall, G. H.; Natoff, I. L.; Vallance, D. K. (1965). "Pharmacological properties of 3-dimethylamino-2-methyl-1-phenyl-1-o-tolylpropanol (SK&F 70463-A)". Journal of Pharmacy and Pharmacology. 17 (8): 509–516. doi:10.1111/j.2042-7158.1965.tb07713.x
  8. ^ Robert Geoffrey Willi Spickett, et al. GB1039454 (1966 to Smith Kline and French Laboratories Ltd).
  9. ^ Janssen, Paul; Jageneau, Anton H. M.; Demoen, Paul J. A.; van De Westeringh, Corn.; De Canniere, Julienne H. M.; Raeymaekers, Alfons H. M.; Wouters, Maria; Sanczuk, Stefan; Hermans, Bert K. F. (1960). "Compounds Related to Pethidine--III. Basic Ketones derived from Norpethidine". Journal of Medicinal and Pharmaceutical Chemistry. 2 (3): 271–280. doi:10.1021/jm50010a003.