Valerophenone

Valerophenone
Skeletal formula of valerophenone
Ball-and-stick model of the valerophenone molecule
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 Edit this at Wikidata
UNII
  • InChI=1S/C11H14O/c1-2-3-9-11(12)10-7-5-4-6-8-10/h4-8H,2-3,9H2,1H3 checkY
    Key: XKGLSKVNOSHTAD-UHFFFAOYSA-N checkY
  • 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
  • O=C(c1ccccc1)CCCC
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
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability (yellow): no hazard codeSpecial hazards (white): no code
2
1
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Valerophenone, or butyl phenyl ketone, is an aromatic ketone with the formula C6H5C(O)C4H9. It is a colorless liquid that is soluble in organic solvents. It is usually prepared by the acylation of benzene using valeryl chloride.

Selected reactions

Being prochiral, valerophenone undergoes enantioselective hydrogenation to the corresponding alcohol.

Its photochemistry has been studied.

Valerophenone is also an inhibitor of the enzyme carbonyl reductase.

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. Archived from the original (PDF) on 2019-09-05. Retrieved 2019-09-05.