Abstract

Abstract4‐Amino‐3,5‐dinitroaniline (3) was synthesized by fluorine/amine exchange of 4‐fluoro‐3,5‐dinitroaniline in ethanol. 4‐Diazo‐2,6‐dinitrophenol (Iso‐DDNP, 4) was obtained after nitration in HNO3 (100 %) and acetic anhydrid. 4‐Amino‐2,3,5‐trinitrophenol (7) was obtained by nitration of N‐(4‐acetoxyphenyl)acetamide and deprotection of the amine. Further nitration resulted in 6‐diazo‐3‐hydroxy‐2,4‐dinitrophenol (8). The thermal stability and sensitivity of 4 and 8 toward impact and friction was compared to commercially used DDNP (2‐diazo‐4,6‐dinitrophenol). All target compounds were characterized by single‐crystal X‐ray diffraction, NMR and elemental analysis and DSC. The sensitivities were determined by BAM methods (drophammer and friction tester). The heats of formation were calculated by using CBS‐4M electronic enthalpies and the atomization method. Various detonation parameters such as detonation velocity and pressure were computed by using the EXPLO5 computer code V6.01.

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