Formyl cyanide

Formyl cyanide is a simple organic compound with the formula HCOCN and structure HC(\dO)\sC\tN. It is simultaneously a nitrile (R\sC\tN) and an aldehyde (R\sCH\dO). Formyl cyanide is the simplest member of the acyl cyanide family. It is known to occur in space in the Sgr B2 molecular cloud.

Production
Formyl cyanide was first made through methoxyacetonitrile flash vacuum pyrolysis at 600 °C. The same technique with cinnamyloxyacetonitrile or allyloxyacetonitrile also generates formyl cyanide.

In molecular clouds, formation of formyl cyanide is speculated to result from formaldehyde and the cyanide radical:

In Earth's atmosphere, the pollutant acrylonitrile reacts with hydroxyl radical forming formyl cyanide, hydroperoxyl and formaldehyde:

Reactions
Formyl cyanide reacts rapidly with even trace quantities of water to form formic acid and hydrogen cyanide. In scrupulously dry conditions, the compound instead releases carbon monoxide, with a half-life exceeding 45 h.

Related
By formally substituting the hydrogen atom, cyanoformyl chloride, ClC(O)CN, and cyanoformyl bromide, BrC(O)CN are obtained.