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A13776 Diethyl ethoxymethylenemalonate, 98+%

Numéro de CAS
Ethoxymethylenemalonic acid diethyl ester
Ethoxymethylenepropanedioic acid diethyl ester

Stock No. Conditionnement Prix ($) Quantité Disponibilité
A13776-18 50g 19,20
A13776-22 100g 25,50
A13776-30 250g 42,20
A13776-36 500g 75,60
A13776-0B 1000g 144,00
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Diethyl ethoxymethylenemalonate, 98+%


Propriétés chimiques

Poids moleculaire
Point de fusion
Point d'ébullition
Point d'éclair
Indice de réfraction
Storage & Sensitivity
Ambient temperatures.
Miscible with chloroform, dichloromethane and methanol. Immiscible with water.


Diethyl ethoxymethylenemalonate is used for synthesis of pyrido[3,2-e]pyrimido[1,2-c]pyrimidines. Initially, it was used to monitor lysine decarboxylase activity. It is useful in the determination of amino acids by precolumn derivatization by using reversed-phase high-performance liquid chromatography (HPLC). It plays an important role in the Gould-Jacobs reaction to prepare quinolines. For example, anile reacts with this reagent to give 4-hydroxyquinoline. It acts as an intermediate in the production of flumequine, which is a fluoroquinolone antibiotic.


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

Références bibliographiques

Stable equivalent of the ɑ-formylmalonate, valuable synthetic building block, particularly in heterocyclic syntheses. Review: Adv. Het. Chem., 54, (1992).

Can be converted to the unstable diethyl methylenemalonate by catalytic reduction and elimination of ethanol on distillation, see: Org. Synth. Coll., 4, 298 (1963).

Has been used for the protection of the amino group of ɑ-amino acids, allowing clean esterification by O-alkylation. The protecting group can be removed using bromine in chloroform: Synthesis, 544 (1989):

For N-protection of aminoglycosides prior to O-acetylation, see: J. Carbohydr. Chem., 14, 1133 (1995). Chlorine in chloroform at 0oC was used for deprotection.

Kim, Y. H.; Kim, H. J.; Shin, J. H.; Bhatia, S. K.; Seo, H. M.; Kim, Y. G.; Lee, Y. K.; Yang, Y. H.; Park, K. Application of diethyl ethoxymethylenemalonate (DEEMM) derivatization for monitoring of lysine decarboxylase activity. J. Mol. Catal. B: Enzym. 2015, 115, 151-154.

Megias, C.; Giraldo, I. C.; Calle, J. G.; Vioque, J.; Alaiz, M. Determination of l-canavanine and other free amino acids in Vicia disperma (Fabaceae) seeds by precolumn derivatization using diethyl ethoxymethylenemalonate and reversed-phase high-performance liquid chromatography. Talanta 2015, 131, 95-98.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H303-H315-H319-H334-H317

May be harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause allergy or asthma symptoms or breathing difficulties if inhaled. May cause an allergic skin reaction.

Mentions de prudence: P284-P261-P280a-P305+P351+P338-P342+P311a-P501a

Wear respiratory protection. Avoid breathing dust/fume/gas/mist/vapours/spray. 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. If experiencing respiratory symptoms: Call a POISON CENTER/doctor. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Code tarifaire harmonisé


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