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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%

CAS Number
105-53-3
Synonyms
Malonic acid diethyl ester
Propanedioic acid diethyl ester

Size Price ($) Quantity Availability
500g 25.11
2500g 72.18
10000g 249.30
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Diethyl malonate, 99%

MDL
MFCD00009195
EINECS
203-305-9

Chemical Properties

Formula
C7H12O4
Formula Weight
160.17
Melting point
-50°
Boiling Point
198-200°
Flash Point
90°(194°F)
Density
1.055
Refractive Index
1.4140
Solubility
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.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H227

Combustible liquid.

Precautionary Statements: 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.

Other References

Merck
14,3823
Beilstein
774687
Harmonized Tariff Code
2917.19
TSCA
Yes
RTECS
OO0700000

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