3D model (Jmol)
|Molar mass||234.29 g/mol|
|Melting point||*Aldrich 110-111 °C (trans, trans isomer)
|Boiling point||130 °C (266 °F; 403 K) (cis, cis isomer) *Merck|
Except where otherwise noted, 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 pale-yellow solid insoluble in water, but soluble in ethanol. Dibenzylideneacetone is used as a component in sunscreens and as a ligand in organometallic chemistry.
The compound can be prepared in the laboratory through 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).
Reactions and derivatives
Dibenzylideneacetone is a component of the catalyst tris(dibenzylideneacetone)dipalladium(0). It is a labile ligand that is easily displaced by triphenylphosphine, hence it serves a useful entry point into palladium(0) chemistry.
- Conard, C. R.; Dolliver, M. A. (1943). "Dibenzalacetone". Org. Synth.; Coll. Vol., 2, p. 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.