Ethyl acetoacetate

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Ethyl acetoacetate
Ethyl acetoacetate 150px
General
Systematic name Ethyl 3-oxobutanoate
Other names Acetoacetic acid ethyl ester
Ethyl acetylacetate
3-Oxobutanoic acid ethyl ester
Molecular formula C6H10O3
SMILES CC(=O)CC(=O)OCC
Molar mass 130.14 g/mol
Appearance Colourless liquid
with fruit or rum odour
CAS number [141-97-9]
Properties
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
Hazards
MSDS External MSDS
EU classification not listed
NFPA 704
NFPA 704.svg
2
2
0
 
Flash point 70 °C
RTECS number AK5250000
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Related esters Methyl acetoacetate
Ethyl acetate
Diethyl malonate
Related compounds Acetone
Acetylacetone
Diketene
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.

Preparation

Ethyl acetoacetate may be prepared via the Claisen condensation of ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol.

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.

Chemistry

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.

References

Carey, Francis A. (2006). Organic Chemistry (Sixth Edition ed.). New York, NY: McGraw-Hill. ISBN 0-07-111562-5.

External links

de:Acetessigester fi:Etyyliasetoasetaatti


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