Cyanogen azide

"CN4" redirects here. For the nerve, see cranial nerve 4.

Cyanogen azide is a chemical compound with the chemical formula CN₄, or more precisely ⁻N=N⁺=N−C≡N. It is an azide compound of carbon and nitrogen. It 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

Names
Preferred IUPAC name Carbononitridic azide[1]
Other names Cyano azide
Identifiers
CAS Number	764-05-6; Y
3D model (JSmol)	Interactive image
ChemSpider	120351
PubChem CID	136583
UNII	159Y7EZP9V Y
CompTox Dashboard (EPA)	DTXSID30997772
InChI InChI=1S/CN4/c2-1-4-5-3 Key: KWEDUNSJJZVRKR-UHFFFAOYSA-N
SMILES C(#N)N=[N+]=[N-]
Properties
Chemical formula	N3CN
Molar mass	68.039 g·mol−1
Appearance	Colourless oily liquid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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. p. 799. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
2. 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.
5. Marsh, F. D. (September 1972). "Cyanogen azide". The Journal of Organic Chemistry. 37 (19): 2966–2969. doi:10.1021/jo00984a012.
6. Lowe, Derek. "Things I Won't Work With: Cyanogen Azide". Science Translational Medicine. American Association for the Advancement of Science. 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.
8. Michael L. Madigan (13 September 2017). First Responders Handbook: An Introduction, Second Edition. CRC Press. p. 170. ISBN 978-1-351-61207-4.
9. Gordon W. Gribble; J. Joule (3 September 2009). Progress in Heterocyclic Chemistry. Elsevier. pp. 250–1. ISBN 978-0-08-096516-1.
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.
11. Barry M. Trost (1991). Oxidation. Elsevier. p. 479. ISBN 978-0-08-040598-8.
12. 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.

External links

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