dibenzalacetoneen

Dibenzalacetone, often abbreviated as DBA, is an organic compound with the chemical formula C17H14O. It is a solid that is typically yellow in color. DBA is a symmetrical molecule characterized by a central ketone group flanked by two phenyl rings, each substituted with a vinyl group. It exists as three geometric isomers: (E,E), (E,Z), and (Z,Z), with the (E,E) isomer being the most common and stable.

Dibenzalacetone is synthesized through a base-catalyzed aldol condensation reaction between acetone and benzaldehyde. In this reaction, two molecules of benzaldehyde react with one molecule of acetone. This process is a common laboratory experiment for introductory organic chemistry students. The product is often purified by recrystallization.

Due to its conjugated pi system, dibenzalacetone absorbs ultraviolet and visible light, contributing to its yellow color. This property makes it useful as a UV absorber in sunscreens and other cosmetic products. Furthermore, dibenzalacetone is employed as a ligand in organometallic chemistry, particularly in palladium chemistry. It forms stable complexes with palladium, such as tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3), which is a widely used catalyst in various cross-coupling reactions like the Suzuki coupling and Heck reaction. These catalytic applications are crucial in the synthesis of pharmaceuticals, polymers, and fine chemicals.