Propiophenone

Propiophenone

Names
IUPAC name 1-Phenylpropan-1-one
Other names Ethyl phenyl ketone, BzEt
Identifiers
CAS Number	93-55-0
3D model (Jmol)	Interactive image
ChEBI	CHEBI:425902
ChEMBL	ChEMBL193446
ChemSpider	6881
ECHA InfoCard	100.002.053
PubChem	7148
UNII	E599A8OKQH
InChI InChI=1S/C9H10O/c1-2-9(10)8-6-4-3-5-7-8/h3-7H,2H2,1H3 Key: KRIOVPPHQSLHCZ-UHFFFAOYSA-N InChI=1/C9H10O/c1-2-9(10)8-6-4-3-5-7-8/h3-7H,2H2,1H3 Key: KRIOVPPHQSLHCZ-UHFFFAOYAT
SMILES CCC(=O)c1ccccc1
Properties
Chemical formula	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)
Solubility in water	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