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609-09-6 - Diethyl ketomalonate, 95% - Diethyl mesoxalate - Diethyl oxomalonate - A12771 - Alfa Aesar

A12771 Diethyl ketomalonate, 95%

Numéro CAS
609-09-6
Synonymes
Diethyl mesoxalate
Diethyl oxomalonate

Dimensions Prix ($) Quantité Disponibilité
5g 35,36
25g 145,80
100g 507,60
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Diethyl ketomalonate, 95%

MDL
MFCD00009121
EINECS
210-176-2

Propriétés chimiques

Formule
C7H10O5
Poids formulaire
174.15
Point de fusion
ca -70°
Point d'ébullition
208-210°
Point d'éclair
>110°(230°F)
Densité
1.142
Indice de réfraction
1.4150
Sensibilité
Moisture Sensitive
Solubilité
Fully miscible with water.

Applications

Diethyl ketomalonate, reagent employed in Wittig and Aza-Wittig reactions for synthesis of triazoles, and 2-azadienes, respectively.

Notes

Moisture Sensitive. Store in cool dry place in tightly closed container. With good ventilation. Store away from oxidizing agent and water/moisture.

Références bibliographiques

D. Basavaiah; V. V. L. Gownswari. Diethyl Ketomalonate: A Fast Reacting Substrate for Baylis-Hillman Reaction. Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry. 1989,(13-14), 6898-6904.

M. Sugawara; M.M. Baizer. Electrogenerated bases VII. Novel syntheses of ethyl glyoxalate and diethyl ketomalonate via electrogenerated superoxide. Tetrahedron Letters. 1983,24(22), 2223-2226.

The carbonyl group behaves as a heterodienophile towards simple dienes. Curtius degradation of the gem-diester to carbonyl completes a synthesis of ß-unsaturated δ-lactones: Rocz. Chem., 38, 707 (1964); J. Am. Chem. Soc., 97, 6892 (1975); J. Org. Chem., 42, 4095 (1977):

For asymmetric Diels-Alder reaction, see: J. Chem. Soc., Chem. Commun., 676 (1987). For addition to aza-dienes, see: Tetrahedron Lett, 30, 2685 (1989).

Ene-addition to alkenes occurs at the less-substituted carbon. Oxidative degradation leads to ß-unsaturated carboxylic acids: J. Am. Chem. Soc., 102, 2473 (1980); 106, 3797 (1984):

Thus, the reagent could be regarded as a CO2 equivalent in both the above sequences.

Undergoes the Baylis-Hillman reaction in which a carbanionic species, generated by the reversible addition of 1,4-Diazabicyclo[2.2.2]octane, A14003, to a Michael acceptor, adds to the carbonyl group: Synth. Commun., 19, 2461 (1989).

Reacts with activated arenes under Friedel-Crafts conditions, or with aryllithium or Grignard derivatives, to give aryl hydroxymalonates, hydrolysis and decarboxylation of which gives substituted mandelic acids: Org. Synth. Coll., 3, 326 (1955). Alternatively, they may be transformed reductively to arylmalonates and hence to ester enolates: J. Org. Chem., 47, 4692 (1982).

Autres références

Merck
14,5913
Beilstein
971873
Code tarifaire harmonisé
2918.30
TSCA
Yes

Recommandé

Consulté récemment

Produits chimiques

Sciences de la vie

Métaux et matériaux

Catalyseurs

Analytique et matériel de laboratoire