Selective Synthesis and Characterization of the Highly Energetic Materials 1-Hydroxy-5H-tetrazole (CHN4O), its Anion 1-Oxido-5H-tetrazolate (CN4O−) and Bis(1-hydroxytetrazol-5-yl)triazene

Abstract

For the first time, an adequate selective synthesis, circumventing the formation of 2-hydroxy-5H-tetrazole, of 1-hydroxy-5H-tetrazole (HTO), as well as the synthesis of bis(1-hydroxytetrazol-5-yl)triazene (H3T) are reported. Several salts thereof were synthesized and characterized which resulted in the formation of new primary and secondary explosives containing the 1-oxidotetrazolate unit. Molecular structures are characterized by single-crystal X-ray diffraction, 1H and 13C NMR, IR, and elemental analysis. Calculation of the detonation performance using the Explo5 code confirmed the energetic properties of 1-hydroxy-5H-tetrazole. The detonation properties can be adjusted to the requirements for those of a secondary explosive by forming the hydroxylammonium (6) or hydrazinium (7) salts, or to meet the requirements of a primary explosive by forming the silver salt 4, which shows a fast DDT on contact with a flame. The sensitivities of all compounds towards external stimuli such as impact, friction, and electrostatic discharge were measured.