Formyl cyanide is a simple
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the
formula
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
HCOCN and
structure
A structure is an arrangement and organization of interrelated elements in a material object or system, or the object or system so organized. Material structures include man-made objects such as buildings and machines and natural objects such as ...
. It is simultaneously a
nitrile
In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or pr ...
() and an
aldehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
(). Formyl cyanide is the simplest member of the
acyl cyanide
In organic chemistry, an acyl cyanide is a functional group with the Chemical formula, formula and Chemical structure, structure . It consists of an acyl group () attached to cyanide (). Examples include acetyl cyanide, formyl cyanide, and oxal ...
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 of which the density and size permit absorption nebulae, the formation of molecules (most commonly molecular hydrogen, ...
.
Production
Formyl cyanide was first made through
methoxyacetonitrile flash vacuum pyrolysis Flash vacuum pyrolysis (FVP) is a technique in organic synthesis. It entails heating a precursor molecule intensely and briefly. Two key parameters are the temperature and duration (or residence time), which are adjusted to optimize yield, convers ...
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
Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...
and the
cyanide radical
The cyano radical (or cyanido radical) is a radical with molecular formula CN, sometimes written •CN. The cyano radical was one of the first detected molecules in the interstellar medium, in 1938. Its detection and analysis was influential in a ...
:
:
In Earth's atmosphere, the pollutant
acrylonitrile
Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid. It has a pungent odor of garlic or onions. Its molecular structure consists of a vinyl group () linked to a nitrile (). It is an im ...
reacts with
hydroxyl radical
The hydroxyl radical, •HO, is the neutral form of the hydroxide ion (HO–). Hydroxyl radicals are highly reactive and consequently short-lived; however, they form an important part of radical chemistry. Most notably hydroxyl radicals are pr ...
forming formyl cyanide,
hydroperoxyl
The hydroperoxyl radical, also known as the hydrogen superoxide, is the protonated form of superoxide with the chemical formula HO2, also written HOO•. This species plays an important role in the atmosphere and as a reactive oxygen species ...
and formaldehyde:
:
Reactions
Formyl cyanide reacts rapidly with trace quantities of water to form
formic acid
Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid. It has the chemical formula HCOOH and structure . This acid is an important intermediate in chemical synthesis and occurs naturally, most notably in some an ...
and
hydrogen cyanide
Hydrogen cyanide (formerly known as prussic acid) is a chemical compound with the chemical formula, formula HCN and structural formula . It is a highly toxic and flammable liquid that boiling, boils slightly above room temperature, at . HCN is ...
.
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