Synthesis and Properties of N¹, N³‐di (2,4‐dinitrophenyl) −2‐fluoro‐1,3‐diamino‐4,6‐ Dinitrobenzene and its Analogues

Abstract Polynitrobenzene compounds are a type of heat‐resistant explosives with excellent thermal stability. This study reported three novel energetic compounds, namely compounds N 1 , N 3 ‐bis(2,4‐dinitrophenyl)‐2‐fluoro‐4,6‐dinitrobenzene‐1,3‐ diamine ( 3 ), 2‐fluoro‐4,6‐dinitro‐N 1 ,N 3 ‐bis(2,4,6‐trinitrophenyl)benzene‐1,3‐ diamine ( 4 ), and 2‐chloro‐4,6‐dinitro‐N 1 ,N 3 ‐bis(2,4,6‐trinitrophenyl)benzene‐1,3‐ diamine ( 6 ). The target compounds were prepared with commercially available 2,3,4‐trifluoronitrobenzene and 2,3,4‐trichloronitrobenzole. The crystalline structures of compounds 3 , 4 , and 6 were determined by single‐crystal X‐ray diffraction, and the crystal densities ( ρ ) were calculated to be 1.7585 g cm −3 , 1.6651 g cm −3 , and 1.7371 g cm −3 , respectively. Based on the calculated standard molar enthalpy of formation and crystal densities, the Chapman–Jouguet detonation properties of 3 , 4 , and 6 were predicted. Their enthalpy of formation ( ΔH f ), detonation velocities ( D ), and detonation pressures ( P ) were in the ranges of 110.1 kJ mol −1 to 349.9 Kj mol −1 , 7264 m s −1 to 7770 m s −1 , and 21.8 GPa to 25.9 GPa, respectively. Notably, the density, thermal decomposition temperature, detonation velocity, detonation pressure, and impact sensitivity value of compound 3 were 1.76 g cm −3 , 313°C, 7546 m s −1 , 24.2 GPa, and 16 J, respectively, suggesting that compound 3 is a high‐performance heat‐resistant explosive.