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688983

Sigma-Aldrich

Ethyl acetoacetate

Arxada quality, ≥99.0% (GC)

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Synonym(s):
Acetoacetic ester
Linear Formula:
CH3COCH2COOC2H5
CAS Number:
Molecular Weight:
130.14
Beilstein:
385838
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor density

4.48 (vs air)

vapor pressure

1 mmHg ( 28.5 °C)

Assay

≥99.0% (GC)

form

liquid

autoignition temp.

580 °F

quality

Arxada quality

expl. lim.

9.5 %

manufacturer/tradename

Arxada AG

impurities

≤0.05% water
≤0.10% acid (as acetic acid)

color

APHA: ≤15

bp

180 °C
181 °C (lit.)

mp

−43 °C (lit.)

solubility

water: soluble 130 g/L at 20 °C

density

1.029 g/mL at 20 °C (lit.)

SMILES string

CCOC(=O)CC(C)=O

InChI

1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3

InChI key

XYIBRDXRRQCHLP-UHFFFAOYSA-N

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This Item
537349W24150463954
Ethyl acetoacetate Arxada quality, ≥99.0% (GC)

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688983

Ethyl acetoacetate

Ethyl acetoacetate ReagentPlus®, 99%

Sigma-Aldrich

537349

Ethyl acetoacetate

Ethyl acetoacetate ≥99%, FCC, FG

Sigma-Aldrich

W241504

Ethyl acetoacetate

Ethyl acetoacetate analytical standard

Supelco

63954

Ethyl acetoacetate

form

liquid

form

-

form

-

form

-

bp

180 °C, 181 °C (lit.)

bp

181 °C (lit.)

bp

181 °C (lit.)

bp

181 °C (lit.)

mp

−43 °C (lit.)

mp

−43 °C (lit.)

mp

−43 °C (lit.)

mp

−43 °C (lit.)

solubility

water: soluble 130 g/L at 20 °C

solubility

water: soluble 130 g/L at 20 °C

solubility

water: soluble 130 g/L at 20 °C

solubility

water: soluble 130 g/L at 20 °C

density

1.029 g/mL at 20 °C (lit.)

density

1.029 g/mL at 20 °C (lit.)

density

1.029 g/mL at 20 °C (lit.)

density

1.029 g/mL at 20 °C (lit.)

Application

Ethyl acetoacetate can undergo:
  • Transesterification with primary and secondary alcohols in the presence of boric acid.
  • Microbial reduction to form (S)-ethyl 3-hydroxybutyrate.
  • C-acylation by acid chlorides in the presence of magnesium chloride and pyridine.
  • Asymmetric biphasic catalytic hydrogenation in the presence of a water-soluble ruthenium-BINAP complex.

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

164.3 °F - closed cup

Flash Point(C)

73.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Production of (+)-(S)-Ethyl 3-Hydroxybutyrate and (−)-(R)-Ethyl 3-Hydroxybutyrate by Microbial Reduction of Ethyl Acetoacetate
Wipf B, et al.
Helvetica Chimica Acta, 66(2), 485-488 (1983)
Hydrogenation of ethyl acetoacetate catalyzed by hydrosoluble BINAP derivatives
Lamouille T, et al.
Tetrahedron Letters, 42(4), 663-664 (2001)
Enantioselective catalytic asymmetric hydrogenation of ethyl acetoacetate in room temperature ionic liquids
Berthod M, et al.
Tetrahedron Asymmetry, 15(14), 2219-2221 (2004)
Boric acid: an efficient and environmentally benign catalyst for transesterification of ethyl acetoacetate
Kondaiah GCM, et al.
Tetrahedron Letters, 49(1), 106-109 (2008)
Procedures for the acylation of diethyl malonate and ethyl acetoacetate with acid chlorides using tertiary amine bases and magnesium chloride.
Rathke MW and Cowan PJ.
The Journal of Organic Chemistry, 50(15), 2622-2624 (1985)

Articles

Knoevenagel Condensation Reaction

Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

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