9195. Tetracyanoethylene

Nomenclature

CAS number: 670-54-2
Ethenetetracarbonitrile; 1,1,2,2-tetracyanoethene; Δ2,2′-bimalononitrile; TCNE.
C6N4; mol wt 128.09.
C 56.26%, N 43.74%.

Description and references

Prepd by debromination of dibromomalononitrile with copper powder in boiling benzene: Cairns et al., J. Am. Chem. Soc. 80, 2775 (1958).

Chemical structure

Properties

Crystals, mp 200°. Begins to sublime at 120°.

Use

In the synthesis of spiro compds, in modified Diels-Alder reactions, as aromatizing agent: Longone, Smith, Tetrahedron Lett. 1962, 205.