98%
Synonyms: 2,4-Pentanedione, diacetylmethane, pentane-2,4-dione, ACAC
CAS Number: 123-54-6
Molecular Weight: 100.12
MDL number: MFCD00008787
This diketone has the formal name 2,4-pentanedione. It is a precursor for the synthesis of acetylacetonates (acac), a common bidentant ligand. It is also a building block for the synthesis of heterocyclic compounds.
Deprotonation: very strong bases can deprotonate acetylacetone twice, starting at C3 as well as C1. The resulting substance can be alkylated at the C-1 atom.
Precursor for the synthesis of heterocycles: Acetylacetone is a multifunctional precursor of heterocycles. Thus, hydrazine gives substituted pyrazoles upon condensation with acetylacetones, and urea gives pyrimidines.
The precursor of the corresponding imino ligands: acetylacetone condenses with amines, giving mono- and di-ketimines, in which one or two oxygen atoms of acetylacetone, respectively, are replaced by an NR group (where R = aryl, alkyl).
Arylation: Acetylacetonate replaces halides from common halogenated benzoic acid. The reaction is catalyzed by copper.
2-BrC6H4CO2H + NaC5H7O2 → 2-(CH3CO)2HC)-C6H4CO2H + NaBr