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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.[2] It is a highly explosive chemical that is soluble in most organic solvents, and normally handled in dilute solution in this form.[2][3][4] It was first synthesised by F. D. Marsh at DuPont in the early 1960s.[2][5] There had been earlier claims of discovering it as a crystalline solid, which were incorrect.[6]
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.[7][8] 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.[9][10][11][6][12][13][14] It can be synthesised at below room temperature from the reaction of sodium azide with either cyanogen chloride[2] or cyanogen bromide,[5] dissolved in a solvent such as acetonitrile; this reaction must be done with care due to the production of shock-sensitive byproducts from trace moisture.[5][12]
^ 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.
^Energetic Materials, Volume 1. Plenum Press. pp. 68–9. ISBN9780306370762.