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Ethyl acetoacetate

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Title: Ethyl acetoacetate  
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Ethyl acetoacetate

Ethyl acetoacetate
Skeletal formula of ethyl acetoacetate
Space-filling model of the ethyl acetoacetate molecule
IUPAC name
Ethyl 3-oxobutanoate
Other names
Acetoacetic acid ethyl ester
Ethyl acetylacetate
3-Oxobutanoic acid ethyl ester
ChemSpider  Y
Jmol-3D images Image
RTECS number AK5250000
Molar mass 130.14 g/mol
Appearance Colourless liquid
Odor fruit or rum
Density 1.021 g/cm3, liquid
Melting point −45 °C (−49 °F; 228 K)
Boiling point 180.8 °C (357.4 °F; 454.0 K)
2.86 g/100 ml (20 °C)
Acidity (pKa) 10.68 (in H2O)
14.2 (in DMSO)
not listed
NFPA 704
Flash point 70 °C (158 °F; 343 K)
Related compounds
Related esters
Methyl acetoacetate
Ethyl acetate
Diethyl malonate
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

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.


  • Preparation 1
  • Reactivity 2
  • See also 3
  • References 4
  • External links 5


Ethyl acetoacetate is produced industrially by treatment of diketene with ethanol.[1]

The preparation of ethyl acetoacetate is a classic laboratory procedure.[2] It is prepared via the Claisen condensation of ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol.

Preparation of ethyl acetoacetate.


Ethyl acetoacetate is subject to Keto-enol tautomerism. Ethyl acetoacetate is often used in the acetoacetic ester synthesis similar to diethyl malonate in the malonic ester synthesis or the Knoevenagel condensation. The protons alpha to carbonyl groups are acidic, and the resulting carbanion can undergo nucleophilic substitution. A subsequent thermal decarboxylation is also possible.[3] Similar to the behavior of acetylacetone, the enolate of ethyl acetoacetate can also serve as a bidentate ligand. For example, it forms purple coordination complexes with iron(III) salts:

Ethyl acetoacetate can also be reduced to ethyl 3-hydroxybutyrate.

See also

  • Fructone, the ethylene glycol ketal of ethyl acetoacetate, an aroma compound


  1. ^ Wilhelm Riemenschneider and Hermann M. Bolt "Esters, Organic" Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a09_565.pub2
  2. ^ J. K. H. Inglis and K. C. Roberts (1926). "Ethyl Acetoacetate".  
  3. ^ Carey, Francis A. (2006). Organic Chemistry (Sixth ed.). New York, NY: McGraw-Hill.  

External links

  • International Chemical Safety Card 1024
  • Inchem properties database
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