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Updated: Jun 14, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Synthesis of C-C bonded trifluoromethyl-based high-energy density materials via the ANRORC mechanism
Parasar Kumar1, Ramling S Mathpati1, Vikas D Ghule2
1Energetic Materials Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur-208016, Uttar Pradesh, India. srinivasd@iitk.ac.in.
Abstract:
A trifluoromethyl group substituted C-C bonded nitrogen rich energetic material 3-(3-nitro-1H-pyrazol-4-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole (4), its hydroxyl amine (5) and 3,6,7-triamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazol-2-ium (6) salts and hydrazinium 5-(3-nitro-1H-pyrazol-4-yl)-3-(trifluoromethyl)-1,2,4-triazol-1-ide (7) were synthesized and fully characterized using infrared spectroscopy (IR), multinuclear magnetic resonance (NMR) spectroscopy (1H, 13C, and 19F), high-resolution mass spectrometry (HRMS), elemental analysis (EA) and differential scanning calorimetry (DSC) studies. Furthermore, compounds 4 and 7 were confirmed using single-crystal X-ray diffraction studies (SC-XRD). All compounds possess good density (1.70-1.80 g cm-3), detonation velocity (6432-7144 m s-1), pressure (16.38-20.31 GPa), and thermal stability (>170 °C). They are insensitive towards mechanical stimuli, impact (IS > 35 J) and friction (FS > 288 N). Overall, due to their balanced performance, these compounds can be a better replacement for presently used explosives such as trinitrotoluene (TNT).
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