Efficient synthesis of the promising energetic material precursor 4-azido-3,5-dinitro-1H-pyrazole with high detonation performance

4-Azido-3,5-dinitro-1H-pyrazole (ADNP) was synthesized in good yield and high purity, with the possibility of large-scale preparation. Based on the reactivity of the acidic proton, the corresponding metal- and nitrogen-containing salts were also prepared by neutralization in alkaline solution. All compounds have positive heats of formation in the range of 122.5 kJ mol−1 to 544.6 kJ mol−1. Structural differences between neutral molecular and ionic compounds were carefully studies to investigate the potential structure-property relationship. In addition, many derivatives were constructed by introducing of high-energy groups into ADNP, and their heats of formation and detonation performances were also predicted by Gaussian 09, further verifying that ADNP has a promising future as a precursor of energetic material.