Ethyl acetoacetate

Ethyl acetoacetate

Names
IUPAC name Ethyl 3-oxobutanoate
Other names Acetoacetic acid ethyl ester Ethyl acetylacetate 3-Oxobutanoic acid ethyl ester
Identifiers
CAS Number	141-97-9 Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL169176 Y
ChemSpider	13865426 Y
ECHA InfoCard	100.005.015
KEGG	C03500 Y
RTECS number	AK5250000
UNII	IZP61H3TB1 Y
InChI InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3 Y Key: XYIBRDXRRQCHLP-UHFFFAOYSA-N Y InChI=1/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3 Key: XYIBRDXRRQCHLP-UHFFFAOYAP
SMILES CCOC(=O)CC(=O)C
Properties
Chemical formula	C6H10O3
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; 453.9 K)
Solubility in water	2.86 g/100 ml (20 °C)
Acidity (pKa)	10.68 (in H2O) 14.2 (in DMSO)
Magnetic susceptibility (χ)	-71.67·10−6 cm3/mol
Hazards
EU classification (DSD)	not listed
NFPA 704	2 2
Flash point	70 °C (158 °F; 343 K)
Related compounds
Related esters	Methyl acetoacetate Ethyl acetate Diethyl malonate
Related compounds	Acetone Acetylacetone Diketene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
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.

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

The preparation of ethyl acetoacetate is a classic laboratory procedure. 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.

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. 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: