Issue 79, 2014

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

Abstract

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, 1H NMR, 13C NMR spectroscopy, MS and elemental analysis. Theoretical calculations showed that the detonation properties of compound 2 (D = 7.78 km sāˆ’1, P = 27.05 GPa) were satisfactory, compared with 2,4,6-trinitrotoluene (TNT, D = 7.21 km sāˆ’1, P = 22.49 GPa).

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

Supplementary files

Article information

Article type
Paper
Submitted
21 May 2014
Accepted
14 Aug 2014
First published
15 Aug 2014

RSC Adv., 2014,4, 42215-42219

Author version available

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

C. Ma, Z. Liu and Q. Yao, RSC Adv., 2014, 4, 42215 DOI: 10.1039/C4RA04796F

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