Chemistry:Cyanogen azide

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Cyanogen azide
Cyanogen azide structure.svg
Cyanogen-azide-from-MW-3D-bs-17.png
Names
Preferred IUPAC name
Carbononitridic azide[1]
Other names
Cyano azide
Identifiers
3D model (JSmol)
UNII
Properties
CN4
Molar mass 68.039 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

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]

References

  1. ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. pp. 799. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4. 
  2. ↑ 2.0 2.1 2.2 2.3 Marsh, F. D.; Hermes, M. E. (October 1964). "Cyanogen Azide". Journal of the American Chemical Society 86 (20): 4506–4507. doi:10.1021/ja01074a071. 
  3. ↑ Goldsmith, Derek (2001). "Cyanogen azide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc268. ISBN 978-0471936237. 
  4. ↑ 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. Thieme. 14 May 2014. p. 5414. ISBN 978-3-13-182284-0. https://books.google.com/books?id=iFeGAwAAQBAJ&pg=PA5414. 
  5. ↑ 5.0 5.1 5.2 Marsh, F. D. (September 1972). "Cyanogen azide". The Journal of Organic Chemistry 37 (19): 2966–2969. doi:10.1021/jo00984a012. 
  6. ↑ 6.0 6.1 Lowe, Derek. "Things I Won't Work With: Cyanogen Azide". American Association for the Advancement of Science. https://www.science.org/content/blog-post/things-i-won-t-work-cyanogen-azide. Retrieved 27 April 2017. 
  7. ↑ Robert Matyáš; Jiří Pachman (12 March 2013). Primary Explosives. Springer Science & Business Media. p. 111. ISBN 978-3-642-28436-6. https://books.google.com/books?id=wfJHAAAAQBAJ&pg=PA111. 
  8. ↑ Michael L. Madigan (13 September 2017). First Responders Handbook: An Introduction, Second Edition. CRC Press. p. 170. ISBN 978-1-351-61207-4. https://books.google.com/books?id=lGE1DwAAQBAJ&pg=PT170. 
  9. ↑ Gordon W. Gribble; J. Joule (3 September 2009). Progress in Heterocyclic Chemistry. Elsevier. pp. 250–1. ISBN 978-0-08-096516-1. https://books.google.com/books?id=pakD9mxF-NMC&pg=PA250. 
  10. ↑ 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. Thieme. 14 May 2014. p. 2082. ISBN 978-3-13-178081-2. https://books.google.com/books?id=jOaIAwAAQBAJ&pg=PA2082-IA60. 
  11. ↑ Barry M. Trost (1991). Oxidation. Elsevier. p. 479. ISBN 978-0-08-040598-8. https://books.google.com/books?id=s76Dd3brvLMC&pg=PA479. 
  12. ↑ 12.0 12.1 Joo, 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. PMID 18615414. 
  13. ↑ 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. 
  14. ↑ Energetic Materials, Volume 1. Plenum Press. pp. 68–9. ISBN 9780306370762. 

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