Propiophenone

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
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 model Interactive image
PubChem 7148
UNII E599A8OKQH YesY
  • InChI=1S/C9H10O/c1-2-9(10)8-6-4-3-5-7-8/h3-7H,2H2,1H3 YesY
    Key: KRIOVPPHQSLHCZ-UHFFFAOYSA-N YesY
  • 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 134.18 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
Vapor pressure {{{value}}}
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).
YesY verify (what is YesYN ?)
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

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 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] Another propiophenone derivative used as a drug is paroxypropione.

With a flowery odor, propiophenone is a component in some perfumes.

References

  1. 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. Lua error in package.lua at line 80: module 'strict' not found.
  3. Lua error in package.lua at line 80: module 'strict' not found.
  4. Lua error in package.lua at line 80: module 'strict' not found.
  5. Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.