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00410

Sigma-Aldrich

Ethyl acetoacetate

puriss. p.a., ≥99.0% (GC)

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Synonym(s):
Acetoacetic ester
Linear Formula:
CH3COCH2COOC2H5
CAS Number:
Molecular Weight:
130.14
Beilstein/REAXYS Number:
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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This Item
688983W241504537349
Ethyl acetoacetate puriss. p.a., ≥99.0% (GC)

00410

Ethyl acetoacetate

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688983

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Ethyl acetoacetate ≥99%, FCC, FG

W241504

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Ethyl acetoacetate ReagentPlus®, 99%

537349

Ethyl acetoacetate

Quality Level

200

Quality Level

200

Quality Level

400

Quality Level

200

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

refractive index

n20/D 1.419

refractive index

-

refractive index

n20/D 1.418-1.421

refractive index

-

mp

−43 °C (lit.)

mp

−43 °C (lit.)

mp

−43 °C (lit.)

mp

−43 °C (lit.)

bp

181 °C (lit.)

bp

180 °C, 181 °C (lit.)

bp

181 °C (lit.)

bp

181 °C (lit.)

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

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

164.3 °F - closed cup

flash_point_c

73.5 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Knoevenagel condensation reaction between benzaldehyde and ethyl acetoacetate in microreactor and membrane microreactor
Lau WN, et al.
Microporous and Mesoporous Materials : The Official Journal of the International Zeolite Association, 115(1-2), 156-163 (2008)
Michael addition of ethyl acetoacetate to α,β -unsaturated oximes in the presence of FeCl3: a novel synthetic route to substituted nicotinic acid derivatives
Chibiryaev AM, et al.
Tetrahedron Letters, 41(41), 8011-8013 (2000)
Mechanochemical Michael reactions of chalcones and azachalcones with ethyl acetoacetate catalyzed by K2CO3 under solvent-free conditions
Zhang Ze, et al.
Chemistry Letters (Jpn), 33(2), 168-169 (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)
Enantioselective catalytic asymmetric hydrogenation of ethyl acetoacetate in room temperature ionic liquids
Berthod M, et al.
Tetrahedron Asymmetry, 15(14), 2219-2221 (2004)

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