High Thermal Stability and Insensitive Fused Triazole-Triazine Trifluoromethyl-Containing Explosives (TFX)

Abstract

A trifluoromethyl-containing fused triazole-triazine energetic molecule, 3-nitro-7-(trifluoromethyl)-1,2,4-triazolo­[5,1-c]-1,2,4-triazin-4-amine (TFX), has been synthesized in three steps from amino guanidine bicarbonate and trifluoroacetic acid. The process was found to be effective, nontoxic, and simple. The X-ray structure analysis of TFX finds that there are inter- and intramolecular hydrogen bonds and π–π interactions in the crystal lattice. TFX with a high density (1.88 g·cm–3) at room temperature, excellent thermal stability (T p = 300.3 °C), moderate energetic performance, and with insensitivity to mechanical stimulation has potential as heat-resistant energetic materials.

Azolo[5,1‐c][1,2,4]triazines and Azoloazapurines: Synthesis, Antimicrobial activity and in silico Studies

“…These results may possibly be explained by an incomplete dissolution of the substance (Scheme 4). According to the method described in the study, [18] compound 4 l (X=N, R 1 =F 3 C) could be synthesized only in 9 % yield.…”

“…[4,5] In particular, derivatives of azolo[5,1c] [1,2,4]triazine-4-amines are known for a pronounced antimicrobial effect [6][7][8][9][10][11][12] and derivatives of 3-nitroazolo[5,1c] [1,2,4]triazines are known for the antiviral activity. [13] However, 3-nitroazolo[5,1-c][1,2,4]triazine-4-amines were previously considered only as high-energy compounds with low sensitivity [14][15][16][17][18][19][20][21] (Figure 1).…”

Thermal stability of azole-rich energetic compounds: their structure, density, enthalpy of formation and energetic properties

“…The introduction of halogen elements such as F atoms can also improve thermal stability; 50 for example, 1,4-bis(dinitromethyl)-3,6-dinitro-1,4-dihydropyrazoleo[4,3- C ]pyrazole exhibits poor stability at room temperature, but the thermal decomposition temperature of 1,4-bis(fluorodinitromethyl)-3,6-dinitro-1,4-dihydropyrazoleo[4,3- c ]pyrazole (1) increased to 213 °C by introducing a F atom, and the detonation velocity and pressure of 1 also reached 8582 m s −1 and 31.7 GPa, respectively, which are comparable to those of TATB (Table 1). 51 Presently, some trifluoromethyl-containing energetic materials have been reported, including 6-(4-(trifluoromethyl)-1 H -1,2,3-triazole-1-yl)1,3,5-triazine-2,4-diamine (2) ( T d = 291 °C), 52 ( Z )-1,2-bis(4-(3-(trifluoromethyl)-1 H -1,2,4-triazole-5-yl)-1,2,5-oxadiazole-3-yl)diazene 1-oxide (3) ( T d = 276 °C), 53 7-nitro-3-(trifluoromethyl)-[1,2,4]triazoleo[5,1- c ][1,2,4]triazin-4-amine (4) ( T d = 300 °C), 54 5-methyl-2-nitro-7-(trifluoromethyl)-[1,2,4]triazoleo[1,5- a ] pyrimidine (5) ( T d = 242 °C), 55 2-nitro-5,7-bis(trifluoromethyl)-[1,2,4]triazoleo [1,5- a ]pyrimidine (6) ( T d = 219 °C), 55 and 3-trifluoromethyl-6-nitroguanyl-1,2,4-triazoleo[4,3- b ][1,2,4,5]tetrazine (7) ( T d = 232 °C). 48 However, the introduction of –CF 3 groups may lead to a reduction in the detonation performance of these materials (Table 1).…”

Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF3CN

“…It has been well established that the introduction of trifluoromethyl into therapeutic compounds can impart beneficial effects to lipophilicity, metabolic stability, conformational preference, and bioavailability [ 9 , 10 , 11 ]. As a consequence, a broad range of protocols for the construction of trifluoromethylated 1,2,4-triazoles have been disclosed [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 ].…”