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Dibenzyl ketone

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Dibenzyl ketone
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name 1,3-Diphenylpropan-2-one
Other names 1,3-Diphenylacetone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.728 Edit this at Wikidata
EC Number
  • 203-000-0
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H14O/c16-15(11-13-7-3-1-4-8-13)12-14-9-5-2-6-10-14/h1-10H,11-12H2Key: YFKBXYGUSOXJGS-UHFFFAOYSA-N
  • InChI=1/C15H14O/c16-15(11-13-7-3-1-4-8-13)12-14-9-5-2-6-10-14/h1-10H,11-12H2Key: YFKBXYGUSOXJGS-UHFFFAOYAS
SMILES
  • O=C(Cc1ccccc1)Cc2ccccc2
Properties
Chemical formula C15H14O
Molar mass 210.276 g·mol
Appearance white solid
Density 1.069 g/cm
Melting point 32 to 34 °C (90 to 93 °F; 305 to 307 K)
Boiling point 330 °C (626 °F; 603 K)
Magnetic susceptibility (χ) -131.7·10 cm/mol
Hazards
Flash point 149.4 °C (300.9 °F; 422.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Dibenzyl ketone, or 1,3-diphenylacetone, is an organic compound composed of two benzyl groups attached to a central carbonyl group. This results in the central carbonyl carbon atom being electrophilic and the two adjacent carbon atoms slightly nucleophilic. For this reason, dibenzyl ketone is frequently used in an aldol condensation reaction with benzil (a dicarbonyl) and base to create tetraphenylcyclopentadienone. Vera Bogdanovskaia is credited with the classification of dibenzyl ketone.

Preparation

Dibenzyl ketone is prepared by ketonic decarboxylation of phenylacetic acid. One method is where phenylacetic acid is reacted with acetic anhydride and anhydrous potassium acetate and refluxed for two hours at 140−150 °C. The mixture is distilled slowly so that the distillate is mostly acetic acid. Carbon dioxide is released in this reaction. The resultant liquid is a mixture of dibenzyl ketone and minor impurities. Heating the mixture above 200−205 °C leads to resinification with a decrease in the yield of the ketone.

References

  1. Hurd, Charles D.; Thomas, Charles L. (1936). "Preparation of Dibenzyl Ketone and Phenylacetone". J. Am. Chem. Soc. 58 (7): 1240. doi:10.1021/ja01298a043.


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