Synthesis and Detonation Properties of 5-Amino-2,4,6-trinitro-1,3-dihydroxy-benzene.

5-Amino-4,6-dinitro-1,3-dihydroxy-benzene () was synthesized through the ring-opening reaction of macrocyclic compound  with the aid of VNS (vicarious nucleophilic substitution of hydrogen) reaction conditions. The mechanism of ring opening of macrocyclic compound  was studied. 5-Amino-2,4,6-trinitro-1,3-dihydroxy-benzene () was obtained after the nitration of in KNO and concentrated sulfuric acid. The thermal stability, sensitivity, and other detonation performances of or were compared to commercially used 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) or 1,3,5-trinitrotriazacyclohexane (RDX), respectively. All target compounds were characterized by using single-crystal X-ray diffraction, NMR spectroscopy, elemental analysis, and differential scanning calorimetry. The sensitivities were determined by using BAM methods (drop-hammer and friction tests). Performance parameters, including heats of formation and detonation properties, were calculated by using Gaussian 03 and EXPLO5 v6.01 programs, respectively. It is worth pointing out that compound  has a remarkable measured density of 2.078 g cm at 298 K. In addition, compound  is more insensitive than RDX (compound : =11 J; RDX: =7 J; is the impact sensitivity).