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A large number of polynitroaromatic compounds have been prepared at the Naval Weapons Center in programs directed toward the synthesis of new dense, powerful, and insensitive energetic materials. This report collates their explosive properties, including density, detonation velocity and pressure, and impact sensitivity, and attempts to identify structure/property correlations. Such correlations will provide greater understanding of energetic materials in general and should a!!ow the rational, scientific identification of desirable target materials for new synthetic programs.

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Hexanitrobenzene and pentanitrobenzene in benzene solution react with hydrogen halides (HC1, HBr, HI, but not HF) at 25 °C to produce high yields of pentanitrohalobenzenes and 2,3,4,6-tetranitrohalobenzenes, respectively. Pentanitrofluorobenzene also reacts readily with HC1 to yield 3-chloro-2,4,5,6-tetranitrofluorobenzene, but the other pentanitrohalobenzenes are much less reactive. 1,2,3,5-and 1,2,4,5-tetranitrobenzenes react rapidly with concentrated hyrochloric or hydrobromic acids at reflux to form picryl halides and l-halo-2,4,5-trinitrobenzenes, respectively; pentanitrotoluene reacts very slowly under these conditions to form 3-halo-2,4,5,6-tetranitrotoluenes in lower yields. The scope and limitations of this regioselective reaction are defined, and comparison is made to related reactions. A mechanism is presented and discussed.Reactions between nitroaromatics and hydrogen halides(1) Part 3: