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537349

Ethyl acetoacetate

ReagentPlus®, 99%

Synonym(s):

EAA, Ethyl 3-oxobutanoate, Acetoacetic ester

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About This Item

Linear Formula:
CH3COCH2COOC2H5
CAS Number:
141-97-9
Molecular Weight:
130.14
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24878213
EC Number:
205-516-1
Beilstein/REAXYS Number:
385838
MDL number:
MFCD00009199
eCl@ss:
39022303
Assay:
99%
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vapor density

4.48 (vs air)

Quality Segment

200

vapor pressure

1 mmHg ( 28.5 °C)

product line

ReagentPlus®

assay

99%

autoignition temp.

580 °F

expl. lim.

9.5 %

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.)

functional group

ester, ketone

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

Application

Ethyl acetoacetate is a versatile reagent that can be used as a nucleophile in alkylation, conjugate addition and condensation reactions. Some of its applications are:
  • Alkylation at the α-carbon of ethyl acetoacetate followed by hydrolysis and decarboxylation can afford a variety of methyl ketones.
  • It also undergoes acylation at the α-carbon in the presence of MgCl2 and pyridine to give synthetically important intermediates.
  • It can be used in Knoevenagel condensation with aliphatic, aromatic, and heteroaromatic aldehydes to produce α-alkylideneacetoacetates.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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Storage Class

10 - Combustible liquids

wgk

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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