Open main menu


  (Redirected from Azidoazide azide)

1-Diazidocarbamoyl-5-azidotetrazole (nicknamed azidoazide azide by chemistry blogger and medicinal chemist Derek Lowe[2]) is a heterocyclic inorganic compound with the formula C2N14.[3] It is an extremely dangerous and sensitive explosive, to the point of detonating from no obvious stimuli. This results in the near impossibility of conducting any sort of analysis of 1-Diazidocarbamoyl-5-azidotetrazole.

IUPAC name
(5-Azido-1H-tetrazol-1-yl)carbonimidic diazide
Systematic IUPAC name
Other names
5-Azido-1-diazidocarbamoyltetrazole Azidoazide azide
3D model (JSmol)
Abbreviations AA
Molar mass 220.120 g·mol−1
Density 1.723 g·cm−3[1]
Melting point 78 °C (172 °F; 351 K)
Boiling point Decomposes at 110 °C
Solubility Soluble in diethyl ether
357 kcal·mol−1[2] (1495 kJ·mol−1)[1]
Explosive data
Shock sensitivity <0.25 J
Friction sensitivity <1 N
Detonation velocity 8960 m·s−1
Main hazards will unpredictably and violently detonate
NFPA 704
Flammability (red): no hazard codeHealth (blue): no hazard codeReactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no codeNFPA 704 four-colored diamond
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references



1-Diazidocarbamoyl-5-azidotetrazole was produced by diazotating triaminoguanidinium chloride with sodium nitrite in ultra-purified water.[3] It can also be synthesized from isocyanogen tetrabromide and sodium azide as demonstrated in 2019.[4]


Nearly any stimulus will cause 1-diazidocarbamoyl-5-azidotetrazole to detonate.[5] When an attempt was made to chart its infrared spectrum using Raman spectroscopy, it exploded.[2]

Stimuli such as heat, radiation or physical shock will cause the compound to detonate. It may also detonate unpredictably and for no apparent reason.


  1. ^ a b Martin, Franz Albert. "Novel Energetic Materials based on 1,5-Diaminotetrazole and 3,5-Diamino-1H-1,2,4-triazole" (PDF). pp. 80–87. Retrieved 24 February 2018.
  2. ^ a b c Lowe, Derek (9 January 2013). "Things I Won't Work With: Azidoazide Azides, More Or Less". Science Magazine. American Association for the Advancement of Science. Retrieved 24 February 2018.
  3. ^ a b Klapötke, Thomas M.; Martin, Franz A.; Stierstorfer, Jörg (26 April 2011). "C2N14: An Energetic and Highly Sensitive Binary Azidotetrazole". Angewandte Chemie International Edition. 50 (18): 4227–4229. doi:10.1002/anie.201100300. PMID 21472944.
  4. ^ "I make C2N14 in my shed (azidoazide azide) - Ex&F". Youtube. Retrieved 11 Aug 2019.
  5. ^ Klapötke, Thomas M.; Krumm, Burkhard; Martin, Franz A.; Stierstorfer, Jörg (2 January 2012). "New Azidotetrazoles: Structurally Interesting and Extremely Sensitive". Chemistry: An Asian Journal. 7 (1): 214–224. doi:10.1002/asia.201100632. PMID 22069147.

See alsoEdit