Efficient synthesis of -methyltetranitropyrrole: A stable, insensitive and high energy melt-castable material

1-Methyl-2,3,4,5-tetranitropyrrole, a potential high energy density material, first reported in 1979 in only 0.28% overall yield, has been synthesized efficiently (in more than 5% overall yield) by following two alternate routes from 1-(triisopropylsilyl)pyrrole and 1-methylpyrrole. Detailed charact...

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Published in:New journal of chemistry 2019-08, Vol.43 (31), p.12318-12324
Main Authors: Thaltiri, Vikranth, Chavva, Kurumurthy, Kumar, B. Sathish, Panda, Pradeepta K
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Summary:1-Methyl-2,3,4,5-tetranitropyrrole, a potential high energy density material, first reported in 1979 in only 0.28% overall yield, has been synthesized efficiently (in more than 5% overall yield) by following two alternate routes from 1-(triisopropylsilyl)pyrrole and 1-methylpyrrole. Detailed characterization shows that it is stable up to 196 C and possesses a density of 1.93 g cm 3 . The corresponding velocity of detonation and detonation pressure are 8950 m s 1 and 36.9 GPa, respectively. These values are slightly better than those of RDX, whereas, its sensitivity towards impact and friction are much lower than that of RDX. In addition, its melting point of 100 C further highlights its potential as a melt castable material in a high energy formulation. 1-Methyl-2,3,4,5-tetranitropyrrole is the first pyrrole based stable and insensitive high energy density material at par or slightly better than RDX.
ISSN:1144-0546
1369-9261
DOI:10.1039/c9nj01227c