Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

537349

Sigma-Aldrich

Ethyl acetoacetate

ReagentPlus®, 99%

Synonym(s):

EAA, Ethyl 3-oxobutanoate, Acetoacetic ester

Sign Into View Organizational & Contract Pricing
All Photos(2)

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Ethyl Acetoacetate.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
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)
Knoevenagel-kondensationen mit titantetrachlorid/base?II: Alkyliden-und arylidenacet-bzw.-nitroessigester bei 0?22?.
Lehnert W
Tetrahedron, 28(3), 663-666 (1972)
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)
Netta Nir et al.
Applied microbiology and biotechnology, 78(4), 659-667 (2008-01-23)
The asymmetric bio-reduction of 4-chloro-acetoacetic-acid-ethyl-ester to the pharmaceutical building block (S)-4-chloro-3-hydroxybutanoate-ethyl-ester requires the utilization of an enantioselective robust biocatalyst. Some of the natural Saccharomyces cerevisiae strains, isolated from Mount Carmel National Park in Israel, were characterized as resistant to environmental
View All Related Papers

Articles

Biginelli Reaction

The Biginelli Reaction is an acid-catalyzed, three-component reaction between an aldehyde, b-ketoester, and urea that produces tetrahydropyrimidones, which have potential pharmaceutical applications.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service