The amino, azido, nitro, and nitrogen-rich azole substituted derivatives of 1H-benzotriazole have been synthesized for energetic material applications. The synthesized compounds were fully characterized by 1H and 13C NMR spectroscopy, IR, MS, and elemental analysis. 5-Chloro-4-nitro-1H-benzo[1,2,3]triazole (2) and 5-azido-4,6-dinitro-1H-benzo[1,2,3]triazole (7) crystallize in the Pca21 (orthorhombic) and P21/c (monoclinic) space group, respectively, as determined by single-crystal X-ray diffraction. Their densities are 1.71 and 1.77 g cm−3, respectively. The calculated densities of the other compounds range between 1.61 and 1.98 g cm−3. The detonation velocity (D) values calculated for these synthesized compounds range from 5.45 to 8.06 km s−1, and the detonation pressure (P) ranges from 12.35 to 28 GPa.