1,1-Diphenylacetone

Chemical compound From Wikipedia, the free encyclopedia

1,1-Diphenylacetone is an organic compound composed of a benzhydryl group and a methyl group attached to a central carbonyl group.

Quick facts Names, Identifiers ...
1,1-Diphenylacetone
Skeletal formula
Skeletal formula
Ball-and-stick model of 1,1-diphenylacetone
Ball-and-stick model of 1,1-diphenylacetone
Van der Waals space filling model of 1,1-diphenylacetone
Van der Waals space filling model of 1,1-diphenylacetone
Names
Preferred IUPAC name
1,1-Diphenylpropan-2-one
Other names
1,1-Diphenylacetone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.189 Edit this at Wikidata
EC Number
  • 212-307-9
  • InChI=1S/C15H14O/c1-12(16)15(13-8-4-2-5-9-13)14-10-6-3-7-11-14/h2-11,15H,1H3
    Key: DBNWBEGCONIRGQ-UHFFFAOYSA-N
  • CC(=O)C(C1=CC=CC=C1)C2=CC=CC=C2
Properties
C15H14O
Molar mass 210.276 g·mol−1
Appearance white solid
Melting point 46 Â°C (115 Â°F; 319 K)
Boiling point 307 Â°C (585 Â°F; 580 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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Preparation

One method is where phenylacetone is dissolved in benzene, reacted with bromine to effect an α-keto bromination and stirred for 3-6 hours. Then this mixture is slowly added to a solution of anhydrous aluminium chloride in benzene to catalyze a Friedel-Crafts alkylation. A lengthy workup of the reaction mixture ends in recrystallization of the product 1,1-diphenylacetone from petroleum ether.[1]

Alternative syntheses:[2][3]

Applications

  1. β-Phenylmethamphetamine
  2. Diphenadione

References

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