1,1'-Azobis(1,2,3,4-tetrazole)
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| Preferred IUPAC name
1,1′-Diazenediyldi(1H-tetrazole) | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C2H2N10 | |
| Molar mass | 166.108 g·mol−1 |
| Appearance | yellow (cis isomer) white (trans isomer) |
| Density | 1.774 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Explosive |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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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 the Ludwig Maximilian University of 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[1] 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. [2]
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.[3] It is too sensitive to be used as a practical explosive[4][5] and is more sensitive than 1-diazidocarbamoyl-5-azidotetrazole which is often erroneously reported as the most sensitive explosive.[6] Like the azo-containing N8 chain of 1,1'-azobis-1,2,3-triazole it also is capable of transforming from the trans to the cis conformation under UV light.[2]
Synthesis
It is synthesized from 1-aminotetrazole in an azo-coupling reaction using sodium dichloroisocyanurate in acetic acid as the oxidation agent.
See also
References
- ^ Li, Y. C.; Qi, C.; Li, S. H.; Zhang, H. J.; Sun, C. H.; Yu, Y. Z.; Pang, S. P. (2010). "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. doi:10.1021/ja103525v. PMID 20715773.
- ^ a b Klapötke, Thomas M.; Piercey, Davin G. (2011). "1,1′-Azobis(tetrazole): A Highly Energetic Nitrogen-Rich Compound with a N10 Chain". Inorg. Chem. 50 (7): 2732–2734. doi:10.1021/ic200071q. PMID 21384800.
- ^ Tang, Y.; Yang, H.; Wu, B.; Ju, X.; Lu, C.; Cheng, G. (2013). "Synthesis and Characterization of a Stable, Catenated N11Energetic Salt". Angewandte Chemie International Edition. 52 (18): 4875–7. Bibcode:2013ACIE...52.4875T. doi:10.1002/anie.201300117. PMID 23554233.
- ^ "Blogroll: BOOM". Nature Chemistry. 3 (5): 339. 2011-05-01. Bibcode:2011NatCh...3..339.. doi:10.1038/nchem.1041. ISSN 1755-4349. Retrieved 2025-08-23 – via www.nature.com.
- ^ Howes, Laura (16 March 2011). "The explosive potential of nitrogen compounds". Chemistry World. Retrieved 2025-08-23.
- ^ Faletto, Joanie (August 1, 2019). "Beware Of Azidoazide Azide, The World's Most Explosive Chemical". Discovery. Retrieved 2025-08-23.