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

A12544 Ethyl acetoacetate, 99+%

Numéro de CAS
141-97-9
Synonymes
Acetoacetic acid ethyl ester
Acetoacetic ester

Conditionnement Prix ($) Quantité Disponibilité
250g 19,80
500g 21,00
2500g 68,20
10000g 250,00
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Ethyl acetoacetate, 99+%

MDL
MFCD00009199
EINECS
205-516-1

Propriétés chimiques

Formule
C6H10O3
Poids moleculaire
130.14
Point de fusion
-43°
Point d'ébullition
180-181°
Point d'éclair
84°(183°F)
Densité
1.025
Indice de réfraction
1.4190
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H227-H303-H319

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

Mentions de prudence: P210u-P280a-P305+P351+P338-P312a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. 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/doctor if you feel unwell. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Merck
14,3758
Beilstein
385838
Code tarifaire harmonisé
2918.30
TSCA
Yes
RTECS
AK5250000

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