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537349

Sigma-Aldrich

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
Beilstein:
385838
EC Number:
205-516-1
MDL number:
MFCD00009199
UNSPSC Code:
12352100
PubChem Substance ID:
24878213
NACRES:
NA.22

vapor density

4.48 (vs air)

Quality Level

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.)

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 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

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

Certificates of Analysis (COA)

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Knoevenagel-kondensationen mit titantetrachlorid/base?II: Alkyliden-und arylidenacet-bzw.-nitroessigester bei 0?22?.
Lehnert W
Tetrahedron, 28(3), 663-666 (1972)
Synthetic Applications of Dealkoxycarbonylations of Malonate Esters, β-Keto Esters, α-Cyano Esters and Related Compounds in Dipolar Aprotic Media-Part II.
Krapcho A P
Synthesis, 1982(11), 893-914 (1982)
Ethyl Acetoacetate.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Procedures for the acylation of diethyl malonate and ethyl acetoacetate with acid chlorides using tertiary amine bases and magnesium chloride.
Rathke MW and Cowan PJ.
The Journal of Organic Chemistry, 50(15), 2622-2624 (1985)
Debasish Bandyopadhyay et al.
Molecules (Basel, Switzerland), 17(3), 2643-2662 (2012-03-07)
The classical Hantzsch reaction is one of the simplest and most economical methods for the synthesis of biologically important and pharmacologically useful 1,4-dihydropyridine derivatives. Bismuth nitrate pentahydrate under microwave irradiation is proven to act as a very efficient catalyst for
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