|Jmol-3D images||Image 1
|Molar mass||234.29 g/mol|
|Boiling point||130 °C (266 °F; 403 K) (cis,cis isomer) *Merck|
|Solubility in water||Insoluble|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
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.
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).
- Conard, C. R.; Dolliver, M. A. (1943), "Dibenzalacetone", Org. Synth.; Coll. Vol. 2: 167
- Rao, G. N.; Janardhana, C.; Ramanathan, V.; Rajesh, T.; Kumar, P. H. (November 2006). "Photochemical Dimerization of Dibenzylideneacetone. A Convenient Exercise in [2+2] Cycloaddition Using Chemical Ionization Mass Spectrometry". J. Chem. Educ. 83 (11): 1667. doi:10.1021/ed083p1667.