Valerophenone

Valerophenone
Names
	Preferred IUPAC name 1-Phenylpentan-1-one
	Other names 1-Phenyl-1-pentanone; Valerophenone; Butyl phenyl ketone; n-Butyl phenyl ketone
Identifiers
CAS Number	1009-14-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:36812 ;
ChEMBL	ChEMBL372105 ;
ChemSpider	59482 ;
ECHA InfoCard	100.012.516
PubChem CID	66093;
UNII	F27Q043NT1 ;
CompTox Dashboard (EPA)	DTXSID0061406 ;
	InChI InChI=1S/C11H14O/c1-2-3-9-11(12)10-7-5-4-6-8-10/h4-8H,2-3,9H2,1H3 Key: XKGLSKVNOSHTAD-UHFFFAOYSA-N ; InChI=1/C11H14O/c1-2-3-9-11(12)10-7-5-4-6-8-10/h4-8H,2-3,9H2,1H3 Key: XKGLSKVNOSHTAD-UHFFFAOYAK;
	SMILES O=C(c1ccccc1)CCCC;
Properties
Chemical formula	C11H14O
Molar mass	162.23 g/mol
Density	0.988 g/cm3
Melting point	−9.4 °C (15.1 °F; 263.8 K)
Boiling point	105 to 107 °C (221 to 225 °F; 378 to 380 K) at 5 mmHg
Hazards
Safety data sheet	External MSDS
NFPA 704 (fire diamond)	1 2
	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

Valerophenone, or butyl phenyl ketone, is an aromatic ketone with the formula C₆H₅C(O)C₄H₇. It is a colorless liquid that is soluble in organic solvents. It is usually prepared by the acylation of benzene using valeryl chloride.[1]

Selected reactions

Being prochiral, valerophenone undergoes enantioselectiive hydrogenation to the corresponding alcohol.[2]

Its photochemistry has been studied.[3][4]

Valerophenone is also an inhibitor of the enzyme carbonyl reductase.[5]

References

Milstein, D.; Stille, J. K. (1978). "A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compounds catalyzed by palladium". Journal of the American Chemical Society. 100 (11): 3636–3638. doi:10.1021/ja00479a077.
Ohkuma, Takeshi; Ooka, Hirohito; Hashiguchi, Shohei; Ikariya, Takao; Noyori, Ryoji (1995). "Practical Enantioselective Hydrogenation of Aromatic Ketones". Journal of the American Chemical Society. 117 (9): 2675–2676. doi:10.1021/ja00114a043.
Klan P.; Janosek J.; Krz Z. (2000). "Photochemistry of valerophenone in solid solutions". Journal of Photochemistry and Photobiology A: Chemistry. 134 (1): 37–44. doi:10.1016/S1010-6030(00)00244-6.
R. G. Zepp; M. M. Gumz; W. L. Miller & H. Gao (1998). "Photoreaction of Valerophenone in Aqueous Solution". J. Phys. Chem. A. 102 (28): 5716–5723. Bibcode:1998JPCA..102.5716Z. doi:10.1021/jp981130l.
Imamura Y, Narumi R, Shimada H (2007). "Inhibition of carbonyl reductase activity in pig heart by alkyl phenyl ketones" (PDF). J Enzyme Inhib Med Chem. 22 (1): 105–9. doi:10.1080/14756360600954023. PMID 17373555. S2CID 30284545.

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[1] Milstein, D.; Stille, J. K. (1978). "A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compounds catalyzed by palladium". Journal of the American Chemical Society. 100 (11): 3636–3638. doi:10.1021/ja00479a077.

[2] Ohkuma, Takeshi; Ooka, Hirohito; Hashiguchi, Shohei; Ikariya, Takao; Noyori, Ryoji (1995). "Practical Enantioselective Hydrogenation of Aromatic Ketones". Journal of the American Chemical Society. 117 (9): 2675–2676. doi:10.1021/ja00114a043.

[3] Klan P.; Janosek J.; Krz Z. (2000). "Photochemistry of valerophenone in solid solutions". Journal of Photochemistry and Photobiology A: Chemistry. 134 (1): 37–44. doi:10.1016/S1010-6030(00)00244-6.

[4] R. G. Zepp; M. M. Gumz; W. L. Miller & H. Gao (1998). "Photoreaction of Valerophenone in Aqueous Solution". J. Phys. Chem. A. 102 (28): 5716–5723. Bibcode:1998JPCA..102.5716Z. doi:10.1021/jp981130l.

[5] Imamura Y, Narumi R, Shimada H (2007). "Inhibition of carbonyl reductase activity in pig heart by alkyl phenyl ketones" (PDF). J Enzyme Inhib Med Chem. 22 (1): 105–9. doi:10.1080/14756360600954023. PMID 17373555. S2CID 30284545.

Valerophenone

Selected reactions

See also

References