Cyanogen azide

{{Redirect|CN4|the nerve|cranial nerve 4}}

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| ImageFile = cyanogen azide structure.svg

| ImageSize = 200px

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| ImageFile2 = Cyanogen-azide-from-MW-3D-bs-17.png

| PIN = Carbononitridic azide{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=799 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}

| OtherNames = Cyano azide

| Section1 = {{Chembox Identifiers

| CASNo = 764-05-6;

| CASNo_Ref = {{cascite|correct|CAS}}

| ChemSpiderID = 120351

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 159Y7EZP9V

| PubChem = 136583

| SMILES = C(#N)N=[N+]=[N-]

| InChI=1S/CN4/c2-1-4-5-3

| InChIKey=KWEDUNSJJZVRKR-UHFFFAOYSA-N

}}

| Section2 = {{Chembox Properties

| Formula = {{chem2|N3CN}}

| C=1|N=4

| Appearance = Colourless oily liquid

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| Section3 = {{Chembox Hazards

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{{Use British English|date=September 2024}}

Cyanogen azide is a chemical compound with the chemical formula {{chem2|CN4|auto=1}}, or more precisely {{chem2|−N\dN+\dN\sC\tN}}. 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.{{cite journal|last1=Marsh|first1=F. D.|last2=Hermes|first2=M. E.|title=Cyanogen Azide|journal=Journal of the American Chemical Society|date=October 1964|volume=86|issue=20|pages=4506–4507|doi=10.1021/ja01074a071}}{{cite book|last1=Goldsmith|first1=Derek|title=Encyclopedia of Reagents for Organic Synthesis|chapter=Cyanogen azide|date=2001|doi=10.1002/047084289X.rc268|isbn=978-0471936237}}{{cite book|title=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|url=https://books.google.com/books?id=iFeGAwAAQBAJ&pg=PA5414|date=14 May 2014|publisher=Thieme|isbn=978-3-13-182284-0|page=5414}} It was first synthesised by F. D. Marsh at DuPont in the early 1960s.{{cite journal|last1=Marsh|first1=F. D.|title=Cyanogen azide|journal=The Journal of Organic Chemistry|date=September 1972|volume=37|issue=19|pages=2966–2969|doi=10.1021/jo00984a012}} 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.{{cite book|author1=Robert Matyáš|author2=Jiří Pachman|title=Primary Explosives|url=https://books.google.com/books?id=wfJHAAAAQBAJ&pg=PA111|date=12 March 2013|publisher=Springer Science & Business Media|isbn=978-3-642-28436-6|page=111}}{{cite book|author=Michael L. Madigan|title=First Responders Handbook: An Introduction, Second Edition|url=https://books.google.com/books?id=lGE1DwAAQBAJ&pg=PT170|date=13 September 2017|publisher=CRC Press|isbn=978-1-351-61207-4|page=170}} 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.{{cite book|author1=Gordon W. Gribble|author2=J. Joule|title=Progress in Heterocyclic Chemistry|url=https://books.google.com/books?id=pakD9mxF-NMC&pg=PA250|date=3 September 2009|publisher=Elsevier|isbn=978-0-08-096516-1|pages=250–1}}{{cite book|title=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|url=https://books.google.com/books?id=jOaIAwAAQBAJ&pg=PA2082-IA60|date=14 May 2014|publisher=Thieme|isbn=978-3-13-178081-2|page=2082}}{{cite book|author=Barry M. Trost|title=Oxidation|url=https://books.google.com/books?id=s76Dd3brvLMC&pg=PA479|year=1991|publisher=Elsevier|isbn=978-0-08-040598-8|page=479}}{{cite web|last1=Lowe|first1=Derek|author-link=Derek Lowe (chemist)|title=Things I Won't Work With: Cyanogen Azide|url=https://www.science.org/content/blog-post/things-i-won-t-work-cyanogen-azide|website=Science Translational Medicine|publisher=American Association for the Advancement of Science|accessdate=27 April 2017}}{{cite journal|last1=Joo|first1=Young-Hyuk|last2=Twamley|first2=Brendan|last3=Garg|first3=Sonali|last4=Shreeve|first4=Jean'ne M.|author-link4=Jean'ne Shreeve|title=Energetic Nitrogen-Rich Derivatives of 1,5-Diaminotetrazole|journal=Angewandte Chemie International Edition|date=4 August 2008|volume=47|issue=33|pages=6236–6239|doi=10.1002/anie.200801886|pmid=18615414}}{{cite journal|last1=Audran|first1=Gérard|last2=Adiche|first2=Chiaa|last3=Brémond|first3=Paul|last4=El Abed|first4=Douniazad|last5=Hamadouche|first5=Mohammed|last6=Siri|first6=Didier|last7=Santelli|first7=Maurice|title=Cycloaddition of sulfonyl azides and cyanogen azide to enamines. Quantum-chemical calculations concerning the spontaneous rearrangement of the adduct into ring-contracted amidines|journal=Tetrahedron Letters|date=March 2017|volume=58|issue=10|pages=945–948|doi=10.1016/j.tetlet.2017.01.081}}{{cite book |title=Energetic Materials, Volume 1 |publisher=Plenum Press |isbn=9780306370762 |pages=68–9}} 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.