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Cyanogen azide, N3CN or CN4, is an azide 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 in the early 1960s.
Cyanogen azide is a primary explosive, 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 or cyanogen bromide, dissolved in a solvent such as acetonitrile; this reaction must be done with care due to the production from trace moisture of shock-sensitive byproducts.
^ abcdMarsh, F. D.; Hermes, M. E. (October 1964). "Cyanogen Azide". Journal of the American Chemical Society. 86 (20): 4506-4507. doi:10.1021/ja01074a071.
^ abJoo, Young-Hyuk; Twamley, Brendan; Garg, Sonali; Shreeve, Jean'ne M. (4 August 2008). "Energetic Nitrogen-Rich Derivatives of 1,5-Diaminotetrazole". Angewandte Chemie International Edition. 47 (33): 6236-6239. doi:10.1002/anie.200801886. PMID18615414.
^Audran, Gérard; Adiche, Chiaa; Brémond, Paul; El Abed, Douniazad; Hamadouche, Mohammed; Siri, Didier; Santelli, Maurice (March 2017). "Cycloaddition of sulfonyl azides and cyanogen azide to enamines. Quantum-chemical calculations concerning the spontaneous rearrangement of the adduct into ring-contracted amidines". Tetrahedron Letters. 58 (10): 945-948. doi:10.1016/j.tetlet.2017.01.081.