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Sodium acetylacetonate

Sodium acetylacetonate is an organic compound with the nominal formula Na[CH(C(O)CH<sub>3</sub>)<sub>2</sub>]. This white, water-soluble solid is the conjugate base of acetylacetone.

Preparation

The compound is prepared by deprotonation of acetylacetone:

NaOH + CH<sub>2</sub>(C(O)CH<sub>3</sub>)<sub>2</sub> → NaCH(C(O)CH<sub>3</sub>)<sub>2</sub> + H<sub>2</sub>O

The anhydrous compound is produced by deprotonation with sodium hydride in an aprotic solvent such as THF:

NaH + CH<sub>2</sub>(C(O)CH<sub>3</sub>)<sub>2</sub> → NaCH(C(O)CH<sub>3</sub>)<sub>2</sub> + H<sub>2</sub>

Reactions

Oxidation of the salt gives tetraacetylethane.

With metal salts, it reacts to give metal acetylacetonate complexes.

Alkylation of sodium acetylacetonate can result in both O-alkylation and C-alkylation. The former gives the enol ether and the latter gives 3-substituted derivative of acetylacetone.

Structure

The structure of the monohydrate has been established by X-ray crystallography. The sodium cation is bonded to the enolate oxygen centers.

References