Formyl cyanide is a simple
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
with the
formula HCOCN and
structure . It is simultaneously a
nitrile
In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix '' cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including me ...
() and an
aldehyde
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group ...
(). Formyl cyanide is the simplest member of the
acyl cyanide
In organic chemistry, an acyl cyanide is a functional group with the formula and structure . It consists of an acyl group () attached to cyanide (). Examples include acetyl cyanide, formyl cyanide, and oxalyl dicyanide. Acyl cyanides are r ...
family. It is known to occur in space in the
Sgr B2 molecular cloud
A molecular cloud, sometimes called a stellar nursery (if star formation is occurring within), is a type of interstellar cloud, the density and size of which permit absorption nebulae, the formation of molecules (most commonly molecular hydroge ...
.
Production
Formyl cyanide was first made by heating
methoxyacetonitrile at 600 °C. Formyl cyanide can also be made by heating cinnamyloxyacetonitrile
or allyloxyacetonitrile.
In molecular clouds, formation of formyl cyanide is speculated to result from
formaldehyde
Formaldehyde ( , ) ( systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section ...
and the
cyanide radical:
:
CH2O + CN^\bullet -> HCOCN + H^\bullet
In Earth's atmosphere, the pollutant
acrylonitrile
Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecular ...
reacts with
hydroxyl radical
The hydroxyl radical is the diatomic molecule . The hydroxyl radical is very stable as a dilute gas, but it decays very rapidly in the condensed phase. It is pervasive in some situations. Most notably the hydroxyl radicals are produced from the ...
forming formyl cyanide,
hydroperoxyl
The hydroperoxyl radical
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and formaldehyde:
:
CH2=CHCN + OH^\bullet + 3/2 O2 -> HO2 + HCOCN + CH2O
Reactions
Formyl cyanide reacts with water to form
formic acid
Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Est ...
and
hydrogen cyanide
Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structure . It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at . HCN is produced on a ...
.
Related
By formally substituting the hydrogen atom, cyanoformyl chloride, ClC(O)CN, and cyanoformyl bromide, BrC(O)CN are obtained.
References
{{Reflist
Acyl cyanides
Nitriles