13butanedione

1,3-Butanedione, also known as acetylacetone, is an organic compound with the chemical formula C4H6O2. It is a beta-diketone, meaning it has two carbonyl groups separated by a single methylene group. This arrangement makes the methylene protons particularly acidic, allowing acetylacetone to readily enolize. In fact, it exists as an equilibrium mixture of keto and enol tautomers, with the enol form often being more stable due to intramolecular hydrogen bonding.

Acetylacetone is a colorless liquid with a pungent odor, though it can sometimes appear slightly yellow. It is soluble in many organic solvents and moderately soluble in water. Its chemical properties are largely dictated by its diketone structure and its ability to form stable complexes with metal ions. This chelating ability makes it a valuable reagent in coordination chemistry, where it is used to form metal acetylacetonates. These complexes find applications as catalysts, drying agents, and in materials science.

Industrially, acetylacetone is produced through several methods, including the condensation of acetone with ethyl acetate or the reaction of isopropenyl acetate with ketene. It serves as a building block in the synthesis of various heterocyclic compounds and pharmaceuticals. Its reactivity also makes it useful as a cross-linking agent and a stabilizer in certain polymer formulations.