Cyanogen azide, N
3CN or CN
4, is an
azide
In chemistry, azide is a linear, polyatomic anion with the formula and structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the formula , containing the azide functional group. The dominant appli ...
compound of carbon and nitrogen which is an oily, colourless liquid at room temperature.
It is a highly explosive chemical that is soluble in most organic solvents, and normally handled in dilute solution in this form.
It was first synthesised by F. D. Marsh at
DuPont
DuPont de Nemours, Inc., commonly shortened to DuPont, is an American multinational chemical company first formed in 1802 by French-American chemist and industrialist Éleuthère Irénée du Pont de Nemours. The company played a major role in ...
in the early 1960s.
Cyanogen azide is a
primary explosive
An explosive (or explosive material) is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An ...
, although it is far too unstable for practical use as an explosive and is extremely dangerous outside dilute solution.
Its use in chemistry has been as a reagent prepared ''in situ'' for use in the synthesis of chemicals such as diaminotetrazoles, either in dilute solution or as a gas at reduced pressure.
It can be synthesised at below room temperature from the reaction of
sodium azide with either
cyanogen chloride
Cyanogen chloride is a highly toxic chemical compound with the formula CNCl. This linear, triatomic pseudohalogen is an easily condensed colorless gas. More commonly encountered in the laboratory is the related compound cyanogen bromide, a room-te ...
or
cyanogen bromide
Cyanogen bromide is the inorganic compound with the formula (CN)Br or BrCN. It is a colorless solid that is widely used to modify biopolymers, fragment proteins and peptides (cuts the C-terminus of methionine), and synthesize other compounds. ...
,
dissolved in a solvent such as
acetonitrile
Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile ( hydrogen cyanide is a simpler nitrile, but the cyanide anion is not clas ...
; this reaction must be done with care due to the production from trace moisture of shock-sensitive byproducts.
References
External links
NIST
{{Cyanides
Organoazides
Nitriles
Pseudohalogens