Propiophenone

Propiophenone
Names
	IUPAC name 1-Phenylpropan-1-one
	Other names Ethyl phenyl ketone, BzEt
Identifiers
CAS Number	93-55-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:425902 ;
ChEMBL	ChEMBL193446 ;
ChemSpider	6881 ;
ECHA InfoCard	100.002.053
PubChem CID	7148;
UNII	E599A8OKQH ;
CompTox Dashboard (EPA)	DTXSID2044470 ;
	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	134.178 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

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

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.

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References

Siegel, H.; Eggersdorfer, M. "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077.
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.
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.
"propiophenone". Merriam-Webster.com. Merriam-Webster. Retrieved 2 June 2012.
Hartung, Walter H.; Crossley, Frank (1936). "Isonitrosopropiophenone". Organic Syntheses. 16: 44. doi:10.15227/orgsyn.016.0044.; Collective Volume, 2, p. 363

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[ketones-1] Siegel, H.; Eggersdorfer, M. "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