Dibenzylideneacetone

Dibenzylideneacetone
Dibenzylideneacetone
Identifiers
CAS number 538-58-9 YesY
PubChem 1549622
ChemSpider 1266463 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C17H14O
Molar mass 234.29 g/mol
Appearance Yellow solid
Melting point
  • Aldrich 110-111 ºC (trans,trans isomer)
  • Merck 60ºC (cis,trans isomer)
Boiling point

130ºC(cis,cis isomer) *Merck

Solubility in water Insoluble
Hazards
Main hazards Irritant
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula C17H14O. It is a bright-yellow solid insoluble in water, but soluble in ethanol. Dibenzylideneacetone is used as a sunscreen component and as a ligand in organometallic chemistry, for instance in tris(dibenzylideneacetone)dipalladium(0). In this case, it is a labile ligand that is easily displaced by stronger ligands like triphenylphosphine, hence it serves a useful entry point into palladium(0) chemistry.

Preparation

The compound can be prepared in the laboratory by an aldol condensation of benzaldehyde and acetone with sodium hydroxide in a water/ethanol medium with the exclusive formation of the trans,trans isomer (melting point 110–111 °C).[1]

Dibenzalacetone synthesis

This reaction is frequently encountered in organic chemistry education as a laboratory procedure. The conversion proceeds via the intermediacy of benzylideneacetone.

Prolonged exposure to sunlight converts the compound in a [2+2] cycloaddition to a mixture of four cyclobutane isomers.[2]

References


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