|Ethyl acetoacetate 150px|
|Systematic name||Ethyl 3-oxobutanoate|
|Other names||Acetoacetic acid ethyl ester|
3-Oxobutanoic acid ethyl ester
|Molar mass||130.14 g/mol|
with fruit or rum odour
|Density and phase||1.021 g/cm3, liquid|
|Solubility in water||2.86 g/100 ml (20 °C)|
|Melting point||-45 °C (228 K)|
|Boiling point||180.8 °C (454.0 K)|
|Acidity (pKa)||11 (in H2O)|
14.2 (in DMSO)
|Viscosity||? cP at ? °C|
|Dipole moment||? D|
|EU classification||not listed|
|Flash point||70 °C|
|Supplementary data page|
|n, εr, etc.|
Solid, liquid, gas
|Spectral data||UV, IR, NMR, MS|
|Related esters||Methyl acetoacetate|
|Except where noted otherwise, data are given for|
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references
The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is a solvent, and is used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrene and aminopyrene, and vitamin B1; and also in the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food.
Another method is to use acetyl ketene and ethanol. They directly form Ethyl acetoacetate, and the yield is good, so this method is widely used in industries, but the acetyl ketene is very dangerous.
Ethyl acetoacetate is often used similar to diethyl malonate in the Malonic ester synthesis or the Knoevenagel condensation. The protons alpha to carbonyl groups are easily deprotonated and than the carbanion formed can undergo nucleophilic substitution. A subsequent thermal decarboxylation is also possible.
Carey, Francis A. (2006). Organic Chemistry (Sixth Edition ed.). New York, NY: McGraw-Hill. ISBN 0-07-111562-5.