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8.09622

Sigma-Aldrich

Ethyl acetoacetate

for synthesis

Synonym(s):

Ethyl acetoacetate, EAA, Acetoacetic acid ethyl ester

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About This Item

Empirical Formula (Hill Notation):
C6H10O3
CAS Number:
Molecular Weight:
130.14
MDL number:
UNSPSC Code:
12352108
EC Index Number:
205-516-1
NACRES:
NA.22

vapor pressure

0.26 hPa ( 20 °C)

Quality Level

Assay

≥98.0% (GC)

form

liquid

autoignition temp.

350 °C

potency

3980 mg/kg LD50, oral (Rat)
>5000 mg/kg LD50, skin (Rabbit)

expl. lim.

1.0-54 % (v/v)

pH

4.0 (20 °C, 110 g/L in H2O)

mp

-53.3 °C

transition temp

flash point 73.5 °C

solubility

130.3 g/L

density

1.03 g/cm3 at 20 °C

storage temp.

2-30°C

InChI

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

InChI key

XYIBRDXRRQCHLP-UHFFFAOYSA-N

Application

Ethyl acetoacetate can be used as a reactant to synthesize:
  • 7-hydroxycoumarin derivatives via Pechmann condensation reaction with 1,3-dihydroxybenzene in the presence of acid catalysts.
  • 2,6-disubstituted piperidine alkaloid, (−)-pinidinone via stereoselective α-aminoallylation followed by Grubbs′ olefin cross-metathesis reaction.
  • Michael addition products via Michael addition reaction with chalcones and azachalcones in the presence of a base catalyst.
  • α, β-unsaturated carbonyl compounds via Knoevenagel condensation reaction with glyceraldehyde acetonide in the presence of a base catalyst.

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

Analysis Note

Assay (GC, area%): ≥ 98.0 % (a/a)
Density (d 20 °C/ 4 °C): 1.028 - 1.030
Identity (IR): passes test

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


Certificates of Analysis (COA)

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Synthesis of 7-hydroxycoumarins catalysed by solid acid catalysts
Hoefnagel AJ, et al.
Journal of the Chemical Society. Chemical Communications, (2), 225-226 (1995)
Condensation of glyceraldehyde acetonide with ethyl acetoacetate over Mg, Al-mixed oxides derived from hydrotalcites
Veloso Claudia O, et al.
Microporous and Mesoporous Materials : The Official Journal of the International Zeolite Association, 107(1-2), 23-30 (2008)
An Expeditious Stereoselective Synthesis of (-)-Pinidinone from Ethyl Acetoacetate
Damodar K and Jun Jong-Gab
Bulletin of the Korean Chemical Society,, 37(4), 571-575 (2016)
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)

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