Ethyl acetoacetate
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| Ethyl acetoacetate | |
|---|---|
| Image:Ethyl acetoacetate.png Image:Ethyl acetoacetate-3d.png | |
| 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 |
 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.
Contents |
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, New York, NY: McGraw-Hill. ISBN 0-07-111562-5.
