1-Diazidocarbamoyl-5-azidotetrazole

1-Diazidocarbamoyl-5-azidotetrazole, often informally referred to as azidoazide azide,[4] is a heterocyclic inorganic compound with the formula C2N14.[5] It is an extremely sensitive explosive.

1-Diazidocarbamoyl-5-azidotetrazole
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
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]
Structure[3]
orthorhombic
Pbcn
a = 18.1289, b = 8.2128, c = 11.4021
1697.6
8
Thermochemistry
357 kcal·mol−1[4] (1495 kJ·mol−1)[1]
Explosive data
Shock sensitivity <0.25 J
Friction sensitivity <1 N
Detonation velocity 8960 m·s−1
Hazards
Main hazards will unpredictably and violently detonate-Part of the nitrogen highly energetic compounds family.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis

1-Diazidocarbamoyl-5-azidotetrazole was produced by diazotizing triaminoguanidinium chloride with sodium nitrite in ultra-purified water.[5] Another synthesis uses a metathesis reaction between isocyanogen tetrabromide in acetone and aqueous sodium azide.[2] This first forms isocyanogen tetraazide, the “open” isomer of C2N14, while quickly cyclizes under standard conditions to form a tetrazole ring.[6]

Hazards

Nearly any stimulus, such as heat, radiation, or physical shock, will cause 1-diazidocarbamoyl-5-azidotetrazole to detonate.[7] It may also detonate unpredictably and for no apparent reason. This is part of the high energy nitrogen compound family as the nitrogen atoms do not have strong triple bonds and so are stuck in a high energy state until detonation and then change into a less energetic state. When an attempt was made to chart its infrared spectrum using Raman spectroscopy, it exploded.[4]

References
  1. 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. , "Isocyanogen tetraazide and its preparation", issued 1959-04-14
  3. 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. 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.
  5. 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.
  6. Banert, Klaus; Richter, Sebastian; Schaarschmidt, Dieter; Lang, Heinrich (2013). "Well Known or New? Synthesis and Structure Assignment of Binary C2N14 Compounds Reinvestigated". Angewandte Chemie International Edition. 52 (12): 3499–3502. doi:10.1002/anie.201209170. ISSN 1521-3773. PMID 23404921.
  7. 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.

See also
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