Wikipedia

Valerophenone

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.[1]

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).
☒N verify (what is checkY☒N ?)

Selected reactions

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Being prochiral, valerophenone undergoes enantioselective 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

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References

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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.


 

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