Cyanogen azide explained

Cyanogen azide is a chemical compound with the chemical formula, or more precisely . It is an azide compound of carbon and nitrogen. It 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.^{[1] [2] [3]} It was first synthesised by F. D. Marsh at DuPont in the early 1960s.^[4] There had been earlier claims of discovering it as a crystalline solid, which were incorrect.

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.^{[5] [6]} 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.^{[7] [8] [9] [10] [11] [12] [13]} 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 of shock-sensitive byproducts from trace moisture.

External links

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Notes and References

1. Marsh. F. D.. Hermes. M. E.. Cyanogen Azide. Journal of the American Chemical Society. October 1964. 86. 20. 4506–4507. 10.1021/ja01074a071.
2. Book: Goldsmith. Derek. Encyclopedia of Reagents for Organic Synthesis. Cyanogen azide. 2001. 10.1002/047084289X.rc268. 978-0471936237.
3. Book: Houben-Weyl Methods of Organic Chemistry Vol. E 21e, 4th Edition Supplement: Stereoselective Synthesis: Bond Formation, C-N, C-O, C-P, C-S, C-Se, C-Si, C-Sn, C-Te. 14 May 2014. Thieme. 978-3-13-182284-0. 5414.
4. Marsh. F. D.. Cyanogen azide. The Journal of Organic Chemistry. September 1972. 37. 19. 2966–2969. 10.1021/jo00984a012.
5. Book: Robert Matyáš. Jiří Pachman. Primary Explosives. 12 March 2013. Springer Science & Business Media. 978-3-642-28436-6. 111.
6. Book: Michael L. Madigan. First Responders Handbook: An Introduction, Second Edition. 13 September 2017. CRC Press. 978-1-351-61207-4. 170.
7. Book: Gordon W. Gribble. J. Joule. Progress in Heterocyclic Chemistry. 3 September 2009. Elsevier. 978-0-08-096516-1. 250–1.
8. Book: Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 17: Six-Membered Hetarenes with Two Unlike or More than Two Heteroatoms and Fully Unsaturated Larger-Ring Heterocycles. 14 May 2014. Thieme. 978-3-13-178081-2. 2082.
9. Book: Barry M. Trost. Oxidation. 1991. Elsevier. 978-0-08-040598-8. 479.
10. Web site: Lowe. Derek. Derek Lowe (chemist). Things I Won't Work With: Cyanogen Azide. Science Translational Medicine. American Association for the Advancement of Science. 27 April 2017.
11. Joo. Young-Hyuk. Twamley. Brendan. Garg. Sonali. Shreeve. Jean'ne M.. Jean'ne Shreeve. Energetic Nitrogen-Rich Derivatives of 1,5-Diaminotetrazole. Angewandte Chemie International Edition. 4 August 2008. 47. 33. 6236–6239. 10.1002/anie.200801886. 18615414.
12. Audran. Gérard. Adiche. Chiaa. Brémond. Paul. El Abed. Douniazad. Hamadouche. Mohammed. Siri. Didier. Santelli. Maurice. 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. March 2017. 58. 10. 945–948. 10.1016/j.tetlet.2017.01.081.
13. Book: Energetic Materials, Volume 1 . Plenum Press . 9780306370762 . 68–9.