Dibenzylideneacetone

Dibenzylideneacetone (dba) is an organic compound used in organic synthesis as a ligand in organometallic chemistry. It is notable for its role in the Mizoroki-Heck reaction, a method used for the synthesis of organic compounds.

Structure and Properties

Structure of Dibenzylideneacetone

Dibenzylideneacetone is a yellow crystalline solid with a melting point of 75-77 °C. It is soluble in alcohol and ether, but insoluble in water. The compound is a chelating ligand towards transition metals, forming complexes such as chloro(dimethyl sulfide)gold(I) and palladium(II) complexes.

Synthesis

Dibenzylideneacetone can be synthesized by the condensation reaction of benzaldehyde and acetone in the presence of a base such as sodium hydroxide.

Applications

Dibenzylideneacetone is used as a ligand in the synthesis of organometallic compounds. It is also used in the Mizoroki-Heck reaction, a palladium-catalyzed carbon-carbon bond forming reaction.

Safety

Dibenzylideneacetone may cause eye irritation and skin irritation. It is recommended to handle with care and avoid contact with skin and eyes.

See Also

• Organic synthesis
• Organometallic chemistry
• Mizoroki-Heck reaction