81. Acetylacetone

Nomenclature

CAS number: 123-54-6
2,4-Pentanedione; diacetylmethane.
C5H8O2; mol wt 100.12.
C 59.98%, H 8.05%, O 31.96%.

Description and references

Made by the action of sodium on ethyl acetate and acetone or by the action of anhydrous aluminum chloride on acetyl chloride in the presence of an inert solvent: Combes, Compt. Rend. 103, 814 (1886); Ann. Chim. (Paris) 12, 199 (1887); Claisen, Ber. 38, 695 (1905); Hunt, US 2737528 (1956 to Shawinigan Chem.); Georgieff, US 2834811 (1958); Gattermann-Wieland, Praxis des Organischen Chemikers (de Gruyter, Berlin, 40th ed, 1961) p 219. Toxicity data: Carpenter, J. Ind. Hyg. Toxicol. 31, 343 (1949).

Chemical structure

Properties

Colorless or slightly yellow, flammable liquid; pleasant odor. d 0.976. bp 140.5°. mp 23°. nD20 1.4512. One part dissolves in about 8 parts of water. Miscible with alcohol, benzene, chloroform, ether, acetone, glacial acetic acid. LC50 (4 hrs) in rats: 1000 ppm (Carpenter).

Caution

Mild irritant to skin, mucous membranes.

Use

Forms organometallic complexes which are used as gasoline additives, lubricant additives, driers for varnishes and printer's inks, fungicides, insecticides, colors.