24pentanedione

2,4-Pentanedione, commonly referred to as acetylacetone, is a beta-dicarbonyl compound with the formula CH3-CO-CH2-CO-CH3. In solution it exists in rapid keto–enol tautomerism, with the enol form stabilized by intramolecular hydrogen bonding. This tautomerism underlies many of its chemical behaviors, including its acidity and coordinating properties.

Chemistry and applications: Acetylacetone acts as a bidentate ligand, binding through the two carbonyl oxygen atoms after deprotonation to form metal acetylacetonate complexes (M(acac)2, M(acac)3, and related species). This chelating ability makes it important in coordination chemistry, catalysis, and materials science. It is widely employed as a ligand in analytical chemistry, and as a precursor for metal-organic frameworks and various metal-oxide materials. Its use as a stable, versatile source of the acac− ligand has led to numerous derivatives and related reagents.

Physical properties: It is a colorless liquid at room temperature with relatively low volatility and good solubility in organic solvents. Its enol–keto balance and enolate formation contribute to both its reactivity and its utility as a chelating agent.

Safety: Acetylacetone is flammable and can be irritating to skin, eyes, and the respiratory tract. It should be used with adequate ventilation and appropriate personal protective equipment, and stored away from heat and oxidizers in a cool, dry place. Proper handling minimizes exposure and reduces potential hazards.