1-Diazidocarbamoyl-5-azidotetrazole

1-Diazidocarbamoyl-5-azidotetrazole.png (5-Azido-1H-tetrazol-1-yl)carbonimidoyl diazide 1-Diazidocarbamoyl-5-azidotetrazole 5-Azido-1-diazidocarbamoyltetrazole N-(5-Azido-1H-tetrazol-1-yl)carbonimidic diazide 1306278-47-6 Azidoazide azide https://www.acs.org/content/acs/en/molecule-of-the-week/archive/a/azidoazide-azide.html American Chemical Society en 17 August 2020 13 September 2021 28 October 2020 https://web.archive.org/web/20201028181732/https://www.acs.org/content/acs/en/molecule-of-the-week/archive/a/azidoazide-azide.html live changed correct FDA 78AF7V9M78 101796054 N(=[N+]=[N-])C1=NN=NN1N=C(N=[N+]=[N-])N=[N+]=[N-] AASeptember 2025 30649737 1S/C2N14/c3-11-6-1(7-12-4)10-16-2(8-13-5)9-14-15-16 ROKXTJDNIZBVDB-UHFFFAOYSA-N 2 14 1.723 g·cm−3Martin Franz Albert Novel Energetic Materials based on 1,5-Diaminotetrazole and 3,5-Diamino-1H-1,2,4-triazole https://edoc.ub.uni-muenchen.de/14061/1/Martin_Franz_Albert.pdf 24 February 2018 80–87 16 April 2021 https://web.archive.org/web/20210416094502/https://edoc.ub.uni-muenchen.de/14061/1/Martin_Franz_Albert.pdf live 78 Violent explosion at 110 °C Insoluble Soluble in diethyl ether, acetone, hydrocarbons, chlorinated hydrocarbonsIsocyanogen tetraazide and its preparation 1961-06-27 US 2990412 Olin Mathieson Chemical Corp. Grundmann Christoph J. Schnabel Wilhelm Joseph Klapötke Thomas M. Martin Franz A. Stierstorfer Jörg C2N14: An Energetic and Highly Sensitive Binary Azidotetrazole Angewandte Chemie International Edition 26 April 2011 50 18 4227–4229 10.1002/anie.201100300 21472944 2011ACIE...50.4227K free orthorhombic Pbcn 18.1289 8.2128 11.4021 1697.6 8 357 kcal·mol−1Lowe Derek Things I Won't Work With: Azidoazide Azides, More Or Less https://www.science.org/content/blog-post/things-i-won-t-work-azidoazide-azides-more-or-less Science Magazine American Association for the Advancement of Science 24 February 2018 9 January 2013 7 May 2021 https://web.archive.org/web/20210507110923/https://blogs.sciencemag.org/pipeline/archives/2013/01/09/things_i_wont_work_with_azidoazide_azides_more_or_less live (1495 kJ·mol−1) <0.25 J <1 N 8960 m·s−1 will unpredictably and violently detonate – part of the nitrogen highly energetic compounds family. 1-Diazidocarbamoyl-5-azidotetrazoleSometimes jokingly referred to as azidoazide azide is a heterocyclic inorganic compound with the formula C2N14.Klapötke Thomas M. Martin Franz A. Stierstorfer Jörg C2N14: An Energetic and Highly Sensitive Binary Azidotetrazole Angewandte Chemie International Edition 26 April 2011 50 18 4227–4229 10.1002/anie.201100300 21472944 2011ACIE...50.4227K free It is a highly reactive and extremely sensitive explosive. Synthesis 1-Diazidocarbamoyl-5-azidotetrazole was produced by diazotizing triaminoguanidinium chloride with sodium nitrite in ultra-purified water. Another synthesis uses a metathesis reaction between isocyanogen tetrabromide in acetone and aqueous sodium azide. This first forms isocyanogen tetraazide, the "open" isomer of C2N14, which at room temperature quickly undergoes an irreversible cyclization reaction to form a tetrazole ring.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 10.1002/anie.201209170 23404921 2013ACIE...52.3499B 1521-3773 300px|class=skin-invert-image Properties The C2N14 molecule is a monocyclic tetrazole with three azide groups. This ring form is in equilibrium with isocyanogen tetraazide, an isomeric acyclic structure that has long been known to cyclize quickly to the tetrazole. It is one of a family of high energy nitrogen compounds in which the nitrogen atoms do not have strong triple bonds. This instability makes many such compounds liable to explosive decomposition, releasing nitrogen gas. This tetrazole explosive has a decomposition temperature of 124 °C. It is very sensitive, with an impact sensitivity lower than 0.25 joules. It is, however, less sensitive than nitrogen triiodide and 1,1'-azobis(1,2,3,4-tetrazole). Decomposition can be initiated by only using contact or using a laser beam.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 10.1002/asia.201100632 1861-4728 22069147 27239569 For these reasons, it is often erroneously claimed to be the world's most sensitive compound.Beware Of Azidoazide Azide, The World's Most Explosive Chemical https://www.discovery.com/science/Azidoazide-Azide-Most-Explosive-Chemical 2022-04-05 Discovery en 1,1-Azobis(tetrazole): A Highly Energetic Nitrogen-Rich Compound with a N10 Chain Klapötke Thomas M. Piercey Davin G. Inorg. Chem. 2011 50 7 2732–2734 10.1021/ic200071q 21384800 Notes References External links azidoazide azide uNhVK-2mh6w Synthesis video E3Usu6SPVSg Discussion between discoverer and hobby chemists about the synthesis video Category:Tetrazoles Category:Organoazides Category:Explosive chemicals Category:Inorganic carbon compounds Category:Azines (hydrazine derivatives)