Synthesis and characterization of 1‐methyl‐2,4,5‐trinitroimidazole (MTNI)

Abstract

We have reinvestigated the synthesis of 1-methyl-2,4,5-trinitroimidazole (MTNI; 1), and further characterized its physical properties. It is a promising candidate as an insensitive high explosive. Compound 1 was synthesized from the imidazole (2), via a 5-step sequence of reactions, and subjected to various sensitivity tests for explosives. The structure of 1 was characterized by X-ray diffraction. The crystal is orthorhombic; C 4 H 3 N 5 O 6 , M = 217.11, Z = 8, Pca2 1, a = 8.6183(6) Å, b = 17.7119(12) Å, c = 10.6873(7) Å, V = 1631.38(19) Å 3 , Dc = 1.768 g/cm 3 . The structure was refined to R = 0.0284 for 3201 independent reflections with I > 2σ(I). The molecular structures calculated by high levels of ab initio and density functional theories were in good agreement with those observed by X-ray experiment. According to our preliminary sensitivity tests, 1 was characterized to be intermediate in sensitivity between RDX and TNT. The explosive performances were evaluated theoretically, and were found to be comparable to those of RDX. In addition, owing to its low melting point (82 °C), 1 is believed to be an excellent candidate for inclusion in melt-castable explosives, and may lead to increased explosive power.

The crystal structure of 1-methyl-2,4-dinitro-5-iodoimidazole, C4H3IN4O4

“…Recently, these so called "high energy density materials" have attracted renewed attention in conjunction with their favorable detonation performance [4,5]. As a promising candidate, 1-methyl-2,4,5-trinitroimidazole was synthesized by the nitration of 1-methyl-2,4,5-triiodoimidazole [6,7].…”

Thermal characterization of the promising energetic material TKX-50

“…Five-membered heterocyclic rings (pyrozole, imidazole, triazole, tetrazole) are one kind of important structural units of nitrogen-rich energetic materials [3][4][5][6][7]. Among them, the tetrazole ring possesses the highest nitrogen content, which in turn leads to the highest positive heat of formation and best detonation performance.…”

Quantum chemical study on nitroimidazole, polynitroimidazole and their methyl derivatives

“…Moreover, it can be prepared from the inexpensive starting materials [6]. Besides 2,4-DNI, other polynitro-substituted imidazole derivatives, such as 4,5-dinitroimidazole, 2,4,5-trinitroimidazole, 1-methyl-2,4,5-trinitroimidazole and 4,4 ,5,5 -tetranitro-2,2 -bi-1H-imidazole (TNBI), have also been synthesized and tested as insensitive high energy materials [4,[7][8][9][10][11]. Theorists suggest that the explosive performance of trinitro-substituted imidazoles should be almost close to that of RDX [12].…”