Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula C<sub>17</sub>H<sub>14</sub>O. It is a pale-yellow solid insoluble in water, but soluble in ethanol.
It was first prepared in 1881 by the German chemist Rainer Ludwig Claisen (1851âÂÂ1930) and the Swiss chemist Charles-Claude-Alexandre Claparède (14 April 1858 â 1 November 1913).
The trans,trans isomer can be prepared in high yield and purity by condensation of benzaldehyde and acetone with sodium hydroxide in a water/ethanol medium followed by recrystallization.
This reaction, which proceeds via the intermediacy of benzylideneacetone, is often performed in organic chemistry classes, and is called Claisen-Schmidt condensation.
Prolonged exposure to sunlight initiates [2+2] cycloadditions, converting it to a mixture of dimeric and trimeric cyclobutane cycloadducts.
Dibenzylideneacetone is used as a component in sunscreens and as a ligand in organometallic chemistry.
For example, it 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.