Skip to Content
Merck
All Photos(1)

Key Documents

More Documents

Safety Information

688983

Sigma-Aldrich

Ethyl acetoacetate

Arxada quality, ≥99.0% (GC)

Synonym(s):

Acetoacetic ester

Sign Into View Organizational & Contract Pricing
All Photos(1)

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:
329761207
NACRES:
NA.22

vapor density

4.48 (vs air)

Quality Level

200

vapor pressure

1 mmHg ( 28.5 °C)

Assay

≥99.0% (GC)

form

liquid

autoignition temp.

580 °F

quality

Arxada quality

expl. lim.

9.5 %

manufacturer/tradename

Arxada AG

impurities

≤0.05% water
≤0.10% acid (as acetic acid)

color

APHA: ≤15

bp

180 °C
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 can undergo:
  • Transesterification with primary and secondary alcohols in the presence of boric acid.
  • Microbial reduction to form (S)-ethyl 3-hydroxybutyrate.
  • C-acylation by acid chlorides in the presence of magnesium chloride and pyridine.
  • Asymmetric biphasic catalytic hydrogenation in the presence of a water-soluble ruthenium-BINAP complex.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

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

Hydrogenation of ethyl acetoacetate catalyzed by hydrosoluble BINAP derivatives
Lamouille T, et al.
Tetrahedron Letters, 42(4), 663-664 (2001)
Production of (+)-(S)-Ethyl 3-Hydroxybutyrate and (−)-(R)-Ethyl 3-Hydroxybutyrate by Microbial Reduction of Ethyl Acetoacetate
Wipf B, et al.
Helvetica Chimica Acta, 66(2), 485-488 (1983)
Enantioselective catalytic asymmetric hydrogenation of ethyl acetoacetate in room temperature ionic liquids
Berthod M, et al.
Tetrahedron Asymmetry, 15(14), 2219-2221 (2004)
Boric acid: an efficient and environmentally benign catalyst for transesterification of ethyl acetoacetate
Kondaiah GCM, et al.
Tetrahedron Letters, 49(1), 106-109 (2008)
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)
View All Related Papers

Articles

Knoevenagel Condensation Reaction

Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

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