Ethyl acetoacetate

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Ethyl acetoacetate
IUPAC name

Ethyl 3-oxobutanoate

Other names

Acetoacetic acid ethyl ester
Ethyl acetylacetate
3-Oxobutanoic acid ethyl ester

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
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
 YesY (verify) (what is: YesY/N?)
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.

Preparation

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.


Reactivity

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

References

  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", Org. Synth. ; Coll. Vol. 1: 235 
  3. ↑ Carey, Francis A. (2006). Organic Chemistry (Sixth Edition ed.). New York, NY: McGraw-Hill. ISBN 0-07-111562-5. 

External links

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