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]

Valerophenone
Names
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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.516
UNII
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)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity (yellow): no hazard codeSpecial hazards (white): no code
1
2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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]

See also

References

  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.


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