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00410

Sigma-Aldrich

Ethyl acetoacetate

puriss. p.a., ≥99.0% (GC)

Synonym(s):
Acetoacetic ester
Linear Formula:
CH3COCH2COOC2H5
CAS Number:
Molecular Weight:
130.14
Beilstein:
385838
EC Number:
MDL number:
eCl@ss:
39022303
PubChem Substance ID:
NACRES:
NA.22

vapor density

4.48 (vs air)

Quality Level

vapor pressure

1 mmHg ( 28.5 °C)

grade

puriss. p.a.

assay

≥99.0% (GC)

autoignition temp.

580 °F

expl. lim.

9.5 %

impurities

≤0.5% water

refractive index

n20/D 1.419

bp

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.)

cation traces

Al: ≤0.5 mg/kg
Ba: ≤0.1 mg/kg
Bi: ≤0.1 mg/kg
Ca: ≤0.5 mg/kg
Cd: ≤0.05 mg/kg
Co: ≤0.02 mg/kg
Cr: ≤0.02 mg/kg
Cu: ≤0.02 mg/kg
Fe: ≤0.1 mg/kg
K: ≤0.5 mg/kg
Li: ≤0.1 mg/kg
Mg: ≤0.1 mg/kg
Mn: ≤0.02 mg/kg
Mo: ≤0.1 mg/kg
Na: ≤0.5 mg/kg
Ni: ≤0.02 mg/kg
Pb: ≤0.1 mg/kg
Sr: ≤0.1 mg/kg
Zn: ≤0.5 mg/kg

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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Application

Ethyl acetoacetate can be used as a reactant in the synthesis of:
  • Knoevenagel condensation products by reacting with α-alkylideneacetoacetate and aliphatic, aromatic, heteroaromatic aldehydes.
  • Michael adducts, via Michael addition reaction with chalcones and azachalcones in the presence of a base catalyst.
  • Substituted nicotinic acid derivatives by treating with α, β-unsaturated oximes via Michael addition followed by ring closure reaction.

It can be also utilized as a reactant in the transesterification and asymmetric hydrogenation reactions to produce valuable products.

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

Certificate of Analysis

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Certificate of Origin

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