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105-53-3 - Diethyl malonate, 99% - Malonic acid diethyl ester - Propanedioic acid diethyl ester - A15468 - Alfa Aesar

A15468 Diethyl malonate, 99%

Numéro CAS
105-53-3
Synonymes
Malonic acid diethyl ester
Propanedioic acid diethyl ester

Dimensions Prix ($) Quantité Disponibilité
500g 25,11
2500g 72,18
10000g 249,30
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Diethyl malonate, 99%

MDL
MFCD00009195
EINECS
203-305-9

Propriétés chimiques

Formule
C7H12O4
Poids formulaire
160.17
Point de fusion
-50°
Point d'ébullition
198-200°
Point d'éclair
90°(194°F)
Densité
1.055
Indice de réfraction
1.4140
Solubilité
Miscible with ethyl alcohol, ether, chloroform and benzene. Slightly miscible with water.

Applications

Diethyl malonate is used in organic synthesis for the preparation of alpha-aryl malonates, mono-substituted and di-substituted acetic acid, barbiturates and artificial flavorings. It is also involved in the synthesis of pharmaceuticals like chloroquine, butazolidin and barbital. It acts as intermediate in the synthesis of vitamin B1, vitamin B6, non-steroidal anti-inflammatory agents agrochemicals and perfumes. In Knoevenagel condensation reaction, it reacts with benzaldehyde to get diethyl benzylidenemalonate.

Notes

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

Références bibliographiques

For phase-transfer monoalkylation of the active methylene group see, e.g. (18-crown-6): Synthesis, 37 (1977); and (BTEAC): Org. Prep. Proced. Int., 26, 469 (1994). Solid-liquid phase transfer alkylation has been promoted by microwave irradiation: Synth. Commun., 25,1761 (1995). Dialkylation can also occur in the presence of BTEAC: Synthesis, 54 (1985); Org. Synth. Coll., 7, 411 (1990), to give cyclopropane derivatives. Stereoselective alkylation has been achieved under particularly mild conditions with secondary alkyl mesylates in the presence of Cesium fluoride, 12885 in DMF; complete inversion occurs at the secondary alkyl carbon: J. Org. Chem., 60, 2627 (1995); see also: Synlett, 499 (1998).

Substituents can also be introduced by Michael addition; see e.g.: Org. Synth. Coll., 8, 467 (1993).

Arylation occurs with aryl bromides in the presence of CuI: Gazz. Chim. Ital., 122, 511 (1992).

C-Acylation of malonic esters is normally carried out by reaction of the Mg derivative with an acid chloride. A convenient method using a combination of MgCl2 and triethylamine was introduced by Rathke: J. Org. Chem., 50, 2622 (1985); see also Triethyl­amine, A12646 for discussion of this system:

A number of procedures have been devised for the direct conversion of malonic esters to acetic esters (decarboalkoxylation), in a single step of which heating in wet DMSO is perhaps the simplest: J. Org. Chem., 43, 138 (1978). See also 1,4-Diazabicyclo[2.2.2]octane, A14003.

Compare also Dimethyl­ malonate, A11007, Di-tert-butyl­ malonate, A12774, Dibenzyl­ malonate, A10844, and Isopropyl­idene malonate, A15603.

Semmes, J. G.; Bevans, S. L.; Mullins, C. H.; Shaughnessy, K. H. Arylation of diethyl malonate and ethyl cyanoacetate catalyzed by palladium/di-tert-butylneopentylphosphine. Tetrahedron Lett. 2015, 56 (23), 3447-3450.

Ramesh, P.; Shalini, B.; Fadnavis, N. W. Knoevenagel condensation of diethylmalonate with aldehydes catalyzed by immobilized bovine serum albumin (BSA). RSC Adv. 2014, 4 (15), 7368-7373.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H227

Combustible liquid.

Mentions de prudence: P210-P280-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. 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.

Autres références

Merck
14,3823
Beilstein
774687
Code tarifaire harmonisé
2917.19
TSCA
Yes
RTECS
OO0700000

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