1-Diazidocarbamoyl-5-azidotetrazole: Difference between revisions
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== Synthesis == |
== Synthesis == |
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1-Diazidocarbamoyl-5-azidotetrazole was produced by [[diazotating]] triaminoguanidinium chloride with [[sodium nitrite]] in ultra-purified [[water]].<ref name="Klapötke 2011" /> Another synthesis uses a metathesis reaction between [[isocyanogen tetrabromide]] and [[sodium azide]].<ref name="patent" /> This first forms isocyanogen tetraazide, the “open” isomer of C<sub>2</sub>N<sub>14</sub>, while quickly cyclizes under standard conditions to form a tetrazole ring.<ref>{{Cite journal|last=Banert|first=Klaus|last2=Richter|first2=Sebastian|last3=Schaarschmidt|first3=Dieter|last4=Lang|first4=Heinrich|date=2013|title=Well Known or New? Synthesis and Structure Assignment of Binary C2N14 Compounds Reinvestigated|url=https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201209170|journal=Angewandte Chemie International Edition|volume=52|issue=12|pages=3499–3502|doi=10.1002/anie.201209170|issn=1521-3773}}</ref> |
1-Diazidocarbamoyl-5-azidotetrazole was produced by [[diazotating]] triaminoguanidinium chloride with [[sodium nitrite]] in ultra-purified [[water]].<ref name="Klapötke 2011" /> Another synthesis uses a metathesis reaction between [[isocyanogen tetrabromide]] in acetone and aqueous [[sodium azide]].<ref name="patent" /> This first forms isocyanogen tetraazide, the “open” isomer of C<sub>2</sub>N<sub>14</sub>, while quickly cyclizes under standard conditions to form a tetrazole ring.<ref>{{Cite journal|last=Banert|first=Klaus|last2=Richter|first2=Sebastian|last3=Schaarschmidt|first3=Dieter|last4=Lang|first4=Heinrich|date=2013|title=Well Known or New? Synthesis and Structure Assignment of Binary C2N14 Compounds Reinvestigated|url=https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201209170|journal=Angewandte Chemie International Edition|volume=52|issue=12|pages=3499–3502|doi=10.1002/anie.201209170|issn=1521-3773}}</ref> |
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== Hazards == |
== Hazards == |
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Revision as of 01:49, 5 March 2020
| 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 | |
CompTox Dashboard (EPA)
|
|
| |
| 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 | |
Std enthalpy of
formation (ΔfH⦵298) |
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) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
 |
1-Diazidocarbamoyl-5-azidotetrazole, often jokingly referred to as Azidoazide Azide[3], is a heterocyclic inorganic compound with the formula C2N14.[4] It is an extremely 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] 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.[5]
Hazards
Nearly any stimulus, such as heat, radiation, or physical shock, will cause 1-diazidocarbamoyl-5-azidotetrazole to detonate.[6] 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, using the isocyanogen tetrabromide and sodium azide method, 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.[7][8][unreliable fringe source?]
References
- ^ 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.
- ^ a b [1], "Isocyanogen tetraazide and its preparation", issued 1959-04-14
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "I make C2N14 in my shed (azidoazide azide) - Ex&F". Youtube. Retrieved 11 Aug 2019.
- ^ ""messing" with Azidoazide Azide". YouTube. Retrieved 19 February 2020.
See also
The dictionary definition of azidoazide azide at Wiktionary
