Synthesis of C-C bonded trifluoromethyl-based high-energy density materials via the ANRORC mechanism

Parasar Kumar; Ramling S Mathpati; Vikas D Ghule; Srinivas Dharavath

doi:10.1039/d4dt02088j

Synthesis of C-C bonded trifluoromethyl-based high-energy density materials via the ANRORC mechanism

Dalton Trans. 2024 Sep 18;53(36):15324-15329. doi: 10.1039/d4dt02088j.

Authors

Parasar Kumar¹, Ramling S Mathpati¹, Vikas D Ghule², Srinivas Dharavath¹

Affiliations

¹ Energetic Materials Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur-208016, Uttar Pradesh, India. srinivasd@iitk.ac.in.
² Department of Chemistry, National Institute of Technology Kurukshetra, Kurukshetra-136119, Haryana, India.

PMID: 39224089
DOI: 10.1039/d4dt02088j

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).