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4,5-Bisnitratomethyl and Similar Representatives of the Rare Class of 2-Nitro-1,2,3-triazoles

Maximilian Benz, Sabrina Dörrich, Thomas M. Klapötke, Tobias Lenz, Mohamed Mouzayek, Jörg Stierstorfer

2023Organic Letters17 citationsDOI

Abstract

A [3+2]-cycloaddition toward bishydroxymethyl-1,2,3-triazole makes the title compound available through selective nitration. The obtained sensitive 2-nitrotriazole was shown to have a high density of 1.764 g cm –3 and a detonation velocity of 8590 m s –1 . It can also be classified as an oxidizer with an oxygen balance toward CO of 12%. Further representatives of this rare class of 2-nitro-1,2,3-triazoles were synthesized. One- and two-dimensional 15 N NMR spectroscopy, crystal structure, and elemental analysis were performed.

Topics & Concepts

ChemistryNitroNitrationCycloadditionElemental analysisDetonationMedicinal chemistryExplosive materialCrystallographyOrganic chemistryCatalysisAlkylEnergetic Materials and CombustionChemical Reactions and MechanismsChemical Reaction Mechanisms
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