acetylacetone

Acetylacetone, also known as 2,4-pentanedione, is a simple beta-dicarbonyl compound with the formula CH3-CO-CH2-CO-CH3. It is a colorless liquid at room temperature that commonly exists in equilibrium with an enol form, which is stabilized by intramolecular hydrogen bonding. The enol tautomer participates in metal coordination and many reactions typical of beta-dicarbonyl compounds.

In coordination chemistry, acetylacetone deprotonates to form the acetylacetonate anion (acac−), a bidentate ligand that chelates metals through the two oxygen atoms. The resulting metal acetylacetonate complexes are widespread and include species such as Fe(acac)3, Ni(acac)2, and Al(acac)3. These complexes are used as catalysts, reactants or intermediates in organic synthesis, and as precursors for materials in coatings, ceramics, and related applications.

Applications of acetylacetone extend to its use as a solvent and as a building block in organic synthesis. It serves as a source of diketone functionality for preparing heterocycles and various derivatives, and its acac ligands enable the stabilization of metal centers in diverse catalytic and preparative contexts.

Safety and handling notes: acetylacetone is a flammable liquid and can be irritant to skin, eyes, and the respiratory tract. It should be used in well-ventilated areas with appropriate personal protective equipment, and stored in a cool, dry location away from incompatible materials.

See also: acetylacetonate, beta-diketones, coordination chemistry.