title: Synthesis and Investigation of Advanced Energetic Materials Based on Bispyrazolylmethanes.
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 (Tdec=310 °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 (Vdet(theor)=9304 m s-1versus Vdet(exp)=9910 m s-1) in the range of that of CL-20. Also, the thermal stability (Tdec=205 °C) and sensitivities of 7 are auspicious. The reaction of 6 with in situ 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).
authors.affiliation: Department of Chemistry, University of Munich (LMU), Butenandtstrasse 5-13 (D), 81377, München, Germany.
authors.forename: Dennis
authors.initials: D
authors.lastname: Fischer
authors.affiliation: RDRL-WML-B, US Army Research Laboratory, Aberdeen Proving Ground, MD, USA.
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Gottfried
authors.affiliation: Department of Chemistry, University of Munich (LMU), Butenandtstrasse 5-13 (D), 81377, München, Germany.
authors.forename: Thomas M
authors.initials: TM
authors.lastname: Klapötke
authors.affiliation: Department of Chemistry, University of Munich (LMU), Butenandtstrasse 5-13 (D), 81377, München, Germany.
authors.forename: Konstantin
authors.initials: K
authors.lastname: Karaghiosoff
authors.affiliation: Department of Chemistry, University of Munich (LMU), Butenandtstrasse 5-13 (D), 81377, München, Germany.
authors.forename: Jörg
authors.initials: J
authors.lastname: Stierstorfer
authors.affiliation: Department of Chemistry, University of Munich (LMU), Butenandtstrasse 5-13 (D), 81377, München, Germany.
authors.forename: Tomasz G
authors.initials: TG
authors.lastname: Witkowski
keywords: X-ray diffraction; diazo compounds; energetic materials; nitrogen heterocycles; pyrazoles