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1-Diazidocarbamoyl-5-azidotetrazole

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1-Diazidocarbamoyl-5-azidotetrazole
File:C2N14.png
Names
IUPAC name
(5-Azido-1H-tetrazol-1-yl)carbonimidic diazide
Systematic IUPAC name
1-Diazidocarbamoyl-5-azidotetrazole
Other names
5-Azido-1-diazidocarbamoyltetrazole
Identifiers
3D model (JSmol)
Abbreviations AA
ChemSpider
  • N(=[N+]=[N-])C1=NN=NN1N=C(N=[N+]=[N-])N=[N+]=[N-]
Properties
C2N14
Molar mass 220.120 g·mol−1
Density 1.723 g·cm−3[1]
Melting point 78 °C (172 °F; 351 K)
Boiling point Violent explosion at 110 °C
Solubility Soluble in diethyl ether, acetone, hydrocarbons, chlorinated hydrocarbons[2]
Thermochemistry
357 kcal·mol−1[3] (1495 kJ·mol−1)[1]
Explosive data
Shock sensitivity <0.25 J
Friction sensitivity <1 N
Detonation velocity 8960 m·s−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 will unpredictably and violently detonate
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth (blue): no hazard codeFlammability (red): no hazard codeInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1-Diazidocarbamoyl-5-azidotetrazole is a heterocyclic inorganic compound with the formula C2N14.[4] 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.

Synthesis

1-Diazidocarbamoyl-5-azidotetrazole was produced by diazotating triaminoguanidinium chloride with sodium nitrite in ultra-purified water.[4]

Hazards

Nearly any stimulus, such as heat, radiation, or physical shock, will cause 1-diazidocarbamoyl-5-azidotetrazole to detonate.[5] It may also detonate unpredictably and for no apparent reason. When an attempt was made to chart its infrared spectrum using Raman spectroscopy, it exploded.[3]

However, at least two chemistry hobbyists have claimed to have produced the compound from isocyanogen tetrabromide and sodium azide following a 1959 patent[2] and documented their results online. Preliminary qualitative observations suggested that although still highly sensitive, the compound is much less so than traditionally described, requiring moderate force to trigger a detonation.[6][7][unreliable fringe source?]

References

  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 [1], "Isocyanogen tetraazide and its preparation", issued 1959-04-14 
  3. ^ a b 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.
  4. ^ 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.
  5. ^ Klapötke, Thomas M.; Krumm, Burkhard; Martin, Franz A.; Stierstorfer, Jörg (2011-11-09). "New Azidotetrazoles: Structurally Interesting and Extremely Sensitive". Chemistry - an Asian Journal. 7 (1): 214–224. doi:10.1002/asia.201100632. ISSN 1861-4728. PMID 22069147.
  6. ^ "I make C2N14 in my shed (azidoazide azide) - Ex&F". Youtube. Retrieved 11 Aug 2019.
  7. ^ ""messing" with Azidoazide Azide". YouTube. Retrieved 19 February 2020.

See also

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