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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

Pricing and availability is not currently available.

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

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This Item
W241512W24150400410
assay

≥98.0% (GC)

assay

≥97%

assay

≥99%

assay

≥99.0% (GC)

Quality Level

200

Quality Level

400

Quality Level

400

Quality Level

200

solubility

130.3 g/L

solubility

water: soluble 35 part, organic solvents: soluble

solubility

water: soluble 130 g/L at 20 °C

solubility

water: soluble 130 g/L at 20 °C

storage temp.

2-30°C

storage temp.

-

storage temp.

-

storage temp.

-

mp

-53.3 °C

mp

−43 °C (lit.)

mp

−43 °C (lit.)

mp

−43 °C (lit.)

density

1.03 g/cm3 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.)

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.[1]
  • 2,6-disubstituted piperidine alkaloid, (−)-pinidinone via stereoselective α-aminoallylation followed by Grubbs′ olefin cross-metathesis reaction.[2]
  • Michael addition products via Michael addition reaction with chalcones and azachalcones in the presence of a base catalyst.[3]
  • α, β-unsaturated carbonyl compounds via Knoevenagel condensation reaction with glyceraldehyde acetonide in the presence of a base catalyst.[4]

It can be also utilized as a reactant in the transesterification and asymmetric hydrogenation reactions to produce valuable products.[5][6]

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

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

164.3 °F - closed cup

flash_point_c

73.5 °C - closed cup


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