Ethoxymethylenemalononitrile

Description

Ethoxymethylenemalononitrile (EMMN) is an orange solid and the melting point of EMMN is 64–66 °C[1].It is an inexpensive reagent. As a functionalized malono-nitrile, it is widely used to synthesize pyrazoles, pyrimidines and a variety of fused heterocyclic systems.

Chemical properties

Off White to Pale Yellow

The Uses of Ethoxymethylenemalononitrile

Chemical intermediate.

The Uses of Ethoxymethylenemalononitrile

Ethoxymethylene Malononitrile (cas# 123-06-8) is a compound useful in organic synthesis.

Preparation

Triethyl orthoformate (67.3 mg, 0.454 mol) and malononitrile (20.0 mg,0.302 mol)  were andded to acetic anhydride (77.2 gm, 0.75 moles) and the mixture was refluxed for 4-5 h at 110-140°C. The reaction was monitored by GC. After the reaction is complete, it is cooled to room temperature. Concentrated the mixture at 70°C at reduced pressure to yield crude solid product and the pure product (Ethoxymethylenemalononitrile) was obtained through purified either by vacuum distillation.

Synthesis Reference(s)

Tetrahedron Letters, 10, p. 3279, 1969 DOI: 10.1017/S0009838800024678

References

[1] Faria J, et al. Ethoxymethylenemalononitrile. Synlett , 2013; 24: 0264–0265.
[2] Maurício , et al. Synthesis and antileishmanial evaluation of 1-aryl-4-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazole derivatives. Bioorganic & Medicinal Chemistry Letters, 2011; 21: 7451-7454.