Synthesis and characterization of 5-amino-1,3,6-trinitro-1H-benzo[d]imidazol-2(3H)-one as an energetic material

被引：1
|
作者：
Ma, Congming [1 ]
Liu, Zuliang [1 ]
Yao, Qizheng [1 ,2 ]
机构：
[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Jiangsu, Peoples R China
[2] China Pharmaceut Univ, Sch Pharm, Nanjing 210009, Jiangsu, Peoples R China
来源：
RSC ADVANCES | 2014年 / 4卷 / 79期
关键词：
MOLECULAR-ORBITAL METHODS; GAUSSIAN-TYPE BASIS; HIGH-PERFORMANCE; DERIVATIVES;
D O I：
10.1039/c4ra04796f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Two synthetic routes for the preparation of 5-amino-1,3,6-trinitro-1H-benzo[d]imidazol-2(3H)-one (2) as an energetic material have been revealed. Direct nitration of 5-amino-1H-benzo[d]imidazol-2(3H)-one (1) gave the trinitrated compound 2 in a poor yield of 11%; and similarly using 1 as starting material, 2 was obtained by N-protected reaction, nitration, deprotection and again nitration reaction with an overall-yield of 48%. All structures of 2 and relevant compounds were determined by IR, H-1 NMR, C-13 NMR spectroscopy, MS and elemental analysis. Theoretical calculations showed that the detonation properties of compound 2 (D = 7.78 km s(-1), P = 27.05 GPa) were satisfactory, compared with 2,4,6-trinitrotoluene (TNT, D = 7.21 km s(-1), P = 22.49 GPa).
引用
收藏
页码：42215 / 42219
页数：5
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