Tuning the synthesis of a dinitroaromatic towards a new trinitroaromatic stabilized energetic material

Abstract

A new isomer of diaminotrinitrobenzene, 3, has been prepared from 1,2-diaminobenzene under high dilution conditions in which the two NH₂ electron-donating groups increase the thermal stability of the 1,2,3-trinitrobenzene backbone. Its thermal decomposition only begins around 230 °C and deflagration occurs at 298 °C, which is of interest for heat-resistant explosives. The crystal structure of the known 1,2-diamino-4,5-dinitrobenzene, 4, which has been obtained in place of 3 under different dilution conditions, is also reported and reveals interesting van der Waals and intermolecular N–H⋯O–N hydrogen-bonding interactions.