Synthesis and Investigation of Advanced Energetic Materials Based on Bispyrazolylmethanes

Fischer, Dennis; Gottfried, Jennifer L.; Klapötke, Thomas M.; Karaghiosoff, Konstantin; Stierstorfer, Jörg and Witkowski, Tomasz G. (2016): Synthesis and Investigation of Advanced Energetic Materials Based on Bispyrazolylmethanes. In: Angewandte Chemie-international Edition, Vol. 55, No. 52: pp. 16132-16135

Abstract

Herein we present the preparation and characterization of three new bispyrazolyl-based energetic compounds with great potential as explosive materials. The reaction of sodium 4-amino-3,5-dinitropyrazolate (5) with dimethyl iodide yielded bis(4-amino-3,5-dinitropyrazolyl)methane (6), which is a secondary explosive with high heat resistance (T-dec=310 degrees C). The oxidation of this compound afforded bis(3,4,5-trinitropyrazolyl)methane (7), which is a combined nitrogen- and oxygen-rich secondary explosive with very high theoretical and estimated experimental detonation performance (V-det (theor)=9304ms(-1) versus V-det(exp)=9910ms(-1)) in the range of that of CL-20. Also, the thermal stability (T-dec=205 degrees C) and sensitivities of 7 are auspicious. The reaction of 6 with insitu generated nitrous acid yielded the primary explosive bis(4-diazo-5-nitro-3-oxopyrazolyl)methane (8), which showed superior properties to those of currently used diazodinitrophenol (DDNP).

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1433-7851
• Language: English