Bis(4-chloro-3,5-dinitro-1H-pyrazol-1-yl)methane 2 was obtained for the first time via the coupling reaction of 4-chloro-3,5-dinitro-1H-pyrazole 1 as a promising precursor for new explosives. The careful selection of the reaction conditions enabled the coupling of 1 having the poor reactivity to produce 2 in a good yield. The target compound, bis(4-azido-3,5-dinitro-1H-pyrazol-1-yl)methane 3, was produced by the double azidation reaction of 2 in one step. Some explosive properties of 2 and 3 were characterized and 3 is expected to be a novel green primary explosive having superior explosive properties and better thermal stability than those of a widely used primary explosive, 2-diazo-4,6-dinitrophenol .

The development of high energy materials (HEMs) with both high explosive performance and decreased sensitivity is a main theme of current research for energetic materials. Polynitroazoles are good building blocks for new energetic materials because of their stable chemical properties. Two new bis(dinitropyrazolyl)methanes as potential insensitive HEMs were prepared via either the coupling of dinitropyrazole or the nitration of bis(mononitropyrazolyl)methane. Their insensitive properties are also reported and compared to those of RDX (trinitrohexahydro‐s‐triazine) and HNIW (CL‐20, hexanitrohexaazaisowurtzitane).