Formyl cyanide

Formyl cyanide is a simple organic compound with the formula HCOCN and structure HC(=O)−C≡N. It is simultaneously a nitrile (R−C≡N) and an aldehyde (R−CH=O). Formyl cyanide is the simplest member of the acyl cyanide family. It is known to occur in space in the Sgr B2 molecular cloud.^[1]

Formyl cyanide

Formyl cyanide
Names
Preferred IUPAC name Formyl cyanide
Systematic IUPAC name Methanoyl cyanide
Other names Cyanoformaldehyde Glyoxylonitrile 2-oxo-acetonitrile oxo-acetonitrile
Identifiers
CAS Number	4471-47-0
3D model (JSmol)	Interactive image
ChemSpider	3068544 Y
PubChem CID	3843063
CompTox Dashboard (EPA)	DTXSID0021549
InChI InChI=1S/C2HNO/c3-1-2-4/h2H Y Key: TUHMQDODLHWPCC-UHFFFAOYSA-N Y
SMILES C(=O)C#N
Properties
Chemical formula	C2HNO
Molar mass	55.036 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Production

Formyl cyanide was first made through methoxyacetonitrile flash vacuum pyrolysis at 600 °C. The same technique with cinnamyloxyacetonitrile^[2] or allyloxyacetonitrile also generates formyl cyanide.^[3][4]

In molecular clouds, formation of formyl cyanide is speculated to result from formaldehyde and the cyanide radical:^[5]

CH₂O + CN• → HCOCN + H•

In Earth's atmosphere, the pollutant acrylonitrile reacts with hydroxyl radical forming formyl cyanide, hydroperoxyl and formaldehyde:^[6]

CH₂=CHCN + HO• + 3⁄2 O₂ → HOO• + HCOCN + CH₂O

Reactions

Formyl cyanide reacts rapidly with trace quantities of water to form formic acid and hydrogen cyanide.^[2]

Related

By formally substituting the hydrogen atom, cyanoformyl chloride, ClC(O)CN, and cyanoformyl bromide, BrC(O)CN are obtained.^[7]