Synthesis and Energetic Properties of 4-Diazo-2,6-dinitrophenol and 6-Diazo-3-hydroxy-2,4-dinitrophenol

Article abstract of DOI:10.1002/ejoc.201500465

4-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. The very sensitive diazophenol derivatives diazo-2,6-dinitrophenol and 6-diazo-3-hydroxy-2,4-dinitrophenol could be synthesized by nitration reactions. They are promising alternatives to the commercially used sensitizer DDNP (2-diazo-4,6-dinitrophenol).