3758. Ethyl Acetoacetate

Nomenclature

CAS number: 141-97-9
3-Oxobutanoic acid ethyl ester; acetoacetic acid ethyl ester; acetoacetic ester; ethyl 3-oxobutanoate.
C6H10O3; mol wt 130.14.
C 55.37%, H 7.75%, O 36.88%.

Description and references

Only the equilibrium mixture of the keto and enol forms is described here. Prepd from ethyl acetate by the action of sodium, sodium ethoxide, sodamide, or calcium: Inglis, Roberts, Org. Synth. coll. vol. I, 235 (2nd ed., 1941); Hansley, Schott, US 2843623 (1958 to Natl. Distillers); Scheibler, Ann. 565, 176 (1949); Gattermann-Wieland, Praxis des Organischen Chemikers (de Gruyter, Berlin, 40th ed., 1961) p 218. Discussion of keto-enol tautomerism: Ward, J. Chem. Educ. 39, 95 (1962). Absorption spectrum: Morton, Rosney, J. Chem. Soc. 1926, 711. Toxicity data: H. F. Smyth et al., J. Ind. Hyg. Toxicol. 31, 60 (1949).

Chemical structure

Properties

Liquid. Agreeable odor. d410 1.0357; d417 1.0288; d425 1.0213; d454 0.9924; d475 0.9703. mp -45°. bp760 180.8°; bp400 158.2°; bp200 138.0°; bp60 106°; bp20 81.1°; bp5 54.0°; bp1.0 28.5°. nD20 1.41937. Flash pt, closed cup: 184°F. Sol in about 35 parts water; misc with the usual organic solvents. LD50 orally in rats: 3.98 g/kg (Smyth).

Caution

Moderately irritating to skin, mucous membranes.