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Facile and selective polynitrations at the 4-pyrazolyl dual backbone: A straightforward access to a series of high-density energetic materials

Abstract

Nitro-functionalized energetic materials are still needed to meet new safety, performance and chemical accessibility demands. The problem of multiple C-nitrations on N-containing heterocycles was resolved successfully for the 4,4-bipyrazole scaffold. A progression of gradually functionalized 3 nitro-4,4-bipyrazole (2), 3,3-dinitro-4,4-bipyrazole (3), 3,5-dinitro-4,4-bipyrazole (4), 3,3,5-trinitro-4,4-bipyrazole (5) and 3,3,5,5-tetranitro-4,4-bipyrazole (6) was obtained in excellent yields by highly selective direct nitrations of 4,4-bipyrazole (1). All synthesized polynitro derivatives 3–6 exhibit high decomposition temperatures of above 290 °C. The introduction of three (5) and four nitro groups (6) into the 4,4-bipyrazole scaffold yields insensitive and thermally stable high explosives with excellent densities and detonation properties. The anhydrous structures of compounds 2–6 were obtained by low-temperature XRD. In addition, the performance of compounds 5 and 6 was investigated with the small scale shock reactivity test.

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Publication details

The article was received on 16 Oct 2018, accepted on 05 Dec 2018 and first published on 06 Dec 2018


Article type: Paper
DOI: 10.1039/C8NJ05266B
Citation: New J. Chem., 2018, Accepted Manuscript
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    Facile and selective polynitrations at the 4-pyrazolyl dual backbone: A straightforward access to a series of high-density energetic materials

    K. V. Domasevitch, I. Gospodinov, H. Krautscheid, T. M. Klapoetke and J. Stierstorfer, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ05266B

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