1,1'-Azobis(1,2,3,4-tetrazole)

442660798 1,1′-azobis(tetrazole).png 200px 1,1′-Diazenediyldi(1H-tetrazole) 1282522-34-2 69817332 1S/C2H2N10/c1-3-5-7-11(1)9-10-12-2-4-6-8-12/h1-2H SETQWLRMPKPJQM-UHFFFAOYSA-N C1=NN=NN1N=NN2C=NN=N2 2 2 10 yellow (cis isomer)white (trans isomer) 1.774 shock-sensitive explosive 1,1'-Azobis(1,2,3,4-tetrazole) is a highly explosive and unstable chemical compound discovered by Thomas M. Klapötke and Davin G. Piercey at LMU Munich which contains a long continuous chain of nitrogen atoms, with an unbroken chain of ten nitrogen atoms contained within two 1,2,3,4-tetrazole rings and an azo bridge. It is related to 1,1'-azobis-1,2,3-triazole Li Y. C. Qi C. Li S. H. Zhang H. J. Sun C. H. Yu Y. Z. Pang S. P. 10.1021/ja103525v 1,1-Azobis-1,2,3-triazole: A High-Nitrogen Compound with Stable N8 Structure and Photochromism Journal of the American Chemical Society 132 35 12172–3 2010 20715773 which has a similar structure but with an 8 nitrogen atom chain through the replacement of two N atoms with C-H groups. It is stable only up to 80 °C and is reported to be one of the most sensitive explosives in existence. 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 we experienced several inadvertent explosions during handling such as allowing the dry powder to slide down the inside of a Raman tube or slowing down the rotation rate of a rotary evaporator as 4 crystallized. The material demands the utmost care in handling, and the sensitivities were well below the measurable limit (<5 N friction and <1 J impact) of our safety characterization equipment; the material violently explodes when impacted with a 150 g hammer at 2 cm (∼0.03 J). It is among the most sensitive materials that we have handled Klapötke and Piercey The ten-nitrogen chain was the record for the longest continuous chain of nitrogen atoms in a chemical compound until Chinese researchers prepared a compound with an 11-nitrogen chain. Tang Y. Yang H. Wu B. Ju X. Lu C. Cheng G. 10.1002/anie.201300117 Synthesis and Characterization of a Stable, Catenated N11Energetic Salt Angewandte Chemie International Edition 52 18 4875–7 2013 23554233 2013ACIE...52.4875T It is too sensitive to be used as a practical explosive2011-05-01 Blogroll: BOOM https://www.nature.com/articles/nchem.1041 Nature Chemistry en 3 5 339 10.1038/nchem.1041 2011NatCh...3..339. 1755-4349 2025-08-23 www.nature.com subscription https://www.chemistryworld.com/news/the-explosive-potential-of-nitrogen-compounds/3003948.article The explosive potential of nitrogen compounds Laura Howes Chemistry World 16 March 2011 2025-08-23 and is more sensitive than 1-diazidocarbamoyl-5-azidotetrazole which is often erroneously reported as the most sensitive explosive.Joanie Faletto August 1, 2019 Beware Of Azidoazide Azide, The World's Most Explosive Chemical https://www.discovery.com/science/Azidoazide-Azide-Most-Explosive-Chemical 2025-08-23 Discovery en Cis‐trans isomerization occurs under UV light exposure. Synthesis It is synthesized from N-aminotetrazole via an azo-coupling reaction using sodium dichloroisocyanurate in acetic acid. thumb|left|300px|1,1'-azobis(tetrazole) synthesis See also HBT (explosive) 1-Diazidocarbamoyl-5-azidotetrazole 1,1'-Azobis-1,2,3-triazole Diazene TKX-50 References Category:Explosive chemicals Category:Tetrazoles Category:Azo compounds Category:Organic compounds with 2 carbon atoms Category:2011 in Germany Category:2011 in science