Cyanoform

Cyanoform (tricyanomethane) is an organic compound with the chemical formula HC(CN)3.

For many years, chemists have been unable to isolate this compound as a neat, free acid.

[2] The reaction of sulfuric acid with sodium tricyanomethanide in water (a reaction first tried by H. Schmidtmann in 1896 with inconclusive results[3]) is reported to result in the formation of hydronium tricyanomethanide [H3O]+[C(CN)3]− or the formation of (Z)-3-amino-2-cyano-3-hydroxyacrylamide, (H2N−)(HO−)C=C(−C≡N)(−C(=O)−NH2), depending on the precise conditions.

[4] The reaction of HCl gas with sodium tricyanomethanide dissolved in THF is reported to yield 1-chloro-1-amino-2,2-dicyanoethylene ((N≡C−)2C=C(−NH2)Cl) and its tautomer.

In September 2015 cyanoform was successfully isolated by a team of scientists at Ludwig Maximilian University of Munich.