Ethyl Acetoacetate

Title: Ethyl Acetoacetate
CAS Registry Number: 141-97-9
CAS Name: 3-Oxobutanoic acid ethyl ester
Additional Names: acetoacetic acid ethyl ester; acetoacetic ester; ethyl 3-oxobutanoate
Molecular Formula: C6H10O3
Molecular Weight: 130.14
Percent Composition: C 55.37%, H 7.75%, O 36.88%
Line Formula: CH3COCH2COOC2H5
Literature 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). Toxicity study: H. F. Smyth et al., J. Ind. Hyg. Toxicol. 31, 60 (1949).
Properties: Liq. 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. Absorption spectrum: Morton, Rosney, J. Chem. Soc. 1926, 711. 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).
Melting point: mp -45°
Boiling point: bp760 180.8°; bp400 158.2°; bp200 138.0°; bp60 106°; bp20 81.1°; bp5 54.0°; bp1.0 28.5°
Flash point: Flash pt, closed cup: 184°F
Index of refraction: nD20 1.41937
Density: d410 1.0357; d417 1.0288; d425 1.0213; d454 0.9924; d475 0.9703
Toxicity data: LD50 orally in rats: 3.98 g/kg (Smyth)
CAUTION: Moderately irritating to skin, mucous membranes.
Ethyl Acrylate Ethyl Alcohol, Denatured Ethyl alpha-Bromopropionate Ethyl alpha-Chloropropionate Ethyl Benzoate

Ethyl acetoacetate
Ethyl acetoacetate
Ethylacetoacetaat-3D.png
Identifiers
CAS number 141-97-9 YesY
ChemSpider 13865426 YesY
UNII IZP61H3TB1 YesY
KEGG C03500 YesY
ChEMBL CHEMBL169176 YesY
RTECS number AK5250000
Jmol-3D images Image 1
Properties
Molecular formula C6H10O3
Molar mass 130.14 g/mol
Appearance Colourless liquid
with fruit or rum odour
Density 1.021 g/cm3, liquid
Melting point -45 °C (228 K)
Boiling point 180.8 °C (454.0 K)
Solubility in water 2.86 g/100 ml (20 °C)
Acidity (pKa) 10.68 (in H2O)
14.2 (in DMSO)
Hazards
EU classification not listed
NFPA 704
NFPA 704.svg
2
2
0
Flash point 70 °C; 158 °F; 343 K
Related compounds
Related esters Methyl acetoacetate
Ethyl acetate
Diethyl malonate
Related compounds Acetone
Acetylacetone
Diketene
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine and aminopyrine, and vitamin B1; as well as the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food.