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A12544 Ethyl acetoacetate, 99+%

CAS Number
141-97-9
Synonyms
Acetoacetic acid ethyl ester
Acetoacetic ester

Stock No. Size Price ($) Quantity Availability
A12544-30 250g 20.60
A12544-36 500g 22.60
A12544-0E 2500g 73.40
A12544-0C 10000g 260.00
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Ethyl acetoacetate, 99+%

MDL
MFCD00009199
EINECS
205-516-1

Chemical Properties

Formula
C6H10O3
Formula Weight
130.14
Melting point
-43°
Boiling Point
180-181°
Flash Point
84°(183°F)
Density
1.025
Refractive Index
1.4190
Storage & Sensitivity
Ambient temperatures.
Solubility
Miscible with water, benzene, chloroform, ether and acetone.

Applications

Ethyl acetoacetate is used as an intermediate in organic synthesis and as a co-promoter for unsaturated polyester resins. It is widely used in the production of dyes, inks, perfumes, plastics and flavoring agents. It is an important starting material for the syntheses of alpha-substituted acetoacetic esters and cyclic compounds like pyrazole, pyrimidine and coumarin derivatives. It acts as an intermediate in the synthesis of vitamins and pharmaceuticals. It finds application as a formaldehyde scavenger.

Notes

Incompatible with acids, bases, oxidizing agents, alkali metals and reducing agents.

Literature References

Under the conditions of the classical acetoacetic ester route to methyl ketones [see, e.g.: Org. Synth. Coll., 1, 248, 351 (1941)], varying amounts of O-alkylation occur. Regioselective C-alkylation can be obtained by phase-transfer procedures: J. Org. Chem., 39, 3271 (1974). For improved alkylation using TBAB, see: Org. Prep. Proced. Int., 26, 469 (1994).

Many techniques have been devised for the decarboalkoxylation of substituted ß-ketoesters (compare Diethyl­ malonate, A15468); for reviews, see: Synthesis, 805, 893 (1982). Enolisable ß-keto esters can be decarboalkoxylated by heating in toluene in the presence of a catalytic amount of DMAP. Other bases are ineffective: J. Org. Chem., 54, 3474 (1989).

For use in diazo transfer reactions, see 4-Acetamidobenzenesulfonyl­ azide, L15916.

Xu, L.; Jiang, Y. G.; Feng, J. Z.; Feng, J. Influence of Ethyl Acetoacetate on the Structure and Thermal Stability of Alumina Aerogel. Mater. Sci. Forum 2015, 816, 157-162.

Dehghan, A.; Singh, S.; Abbasinejad, M. A.; Hassanabadi, A. Four-component reaction between cyanoacetamide, aryl aldehydes, and ethyl acetoacetate with ammonium carbonate. Res. Chem. Intermed. 2015, 41 (2), 1001-1009.

GHS Hazard and Precautionary Statements

Hazard Statements: H227

Combustible liquid.

Precautionary Statements: P210-P280-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,3758
Beilstein
385838
Harmonized Tariff Code
2918.30
TSCA
Yes
RTECS
AK5250000

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