Valerophenone
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]
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| Names | |
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| Preferred IUPAC name
1-Phenylpentan-1-one | |
| Other names
1-Phenyl-1-pentanone Valerophenone Butyl phenyl ketone n-Butyl phenyl ketone | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.012.516 |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| 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) | |
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 | |
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]
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See also
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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