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141-97-9 - Ethyl acetoacetate, 99+% - Acetoacetic acid ethyl ester - Acetoacetic ester - A12544 - Alfa Aesar

A12544 Ethyl acetoacetate, 99+%

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

Size Price ($) Quantity Availability
250g 17.19
500g 21.11
2500g 70.71
10000g 254.41
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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
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: H319-H227-H303

Causes serious eye irritation. Combustible liquid. May be harmful if swallowed.

Precautionary Statements: P210-P280-P264-P305+P351+P338-P312-P337+P313-P370+P378a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. Wash thoroughly after handling. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If eye irritation persists: Get medical advice/attention. In case of fire: Use for extinction: CO2, powder or water spray. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

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

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