21985-87-5Relevant academic research and scientific papers
REACTIONS OF PENTANITROANILINE WITH MONOHYDRIC ALCOHOLS
Kanakina, T. P.,Golod, E. L.,Shugalei, I. V.,Bazanov, A. G.,Tselinskii, I. V.
, p. 481 - 487 (2007/10/02)
The course of reaction between pentanitroaniline and monohydric alcohols is determined by the structure of the alcohol. The reactions of primary and secondary alcohols with pentanitroaniline give 3-alkoxy-2,4,5,6-tetranitroanilines as major products. The reactions of pentanitroaniline with tertiary alcohols give 5-amino-2,3,4,6-tetranitrophenol as the sole product. The reactions of pentanitroaniline with monohydric alcohols proceed through the intermediate formation of a charge-transfer complex and can be treated in terms of a single mechanism both with primary and secondary and with tertiary alcohols.
Synthesis of aminonitrobenzodifuroxan
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, (2008/06/13)
Aminonitrobenzodifuroxan (CL-18) is prepared by directly converting pentanitroaniline to aminonitrobenzodifuroxan with heat in the presence of an excess of sodium azide. The pentanitroaniline is prepared in high yield from 3,5-dinitroaniline with a mixture of nitric acid and sulfuric acid in which the final sulfuric acid concentration is from 99.0 to 99.5%.
Synthesis of Polynitro Compounds. Hexasubstituted Benzenes
Atkins, Ronald L.,Hollins, Richard A.,Wilson, William S.
, p. 3261 - 3266 (2007/10/02)
The synthesis of the three isomeric aminotetranitrotoluenes by nitration of an appriopriate aminodinitrotoluene is presented, and the apparent ipso nitration of 4-amino-2,6-dinitrotoluene to give pentanitroaniline, is also discussed.The oxidation of the isomeric aminotetranitrotoluenes to pentanitrotoluene is described, as is the ammonolysis of pentanitroaniline and of pentanitrotoluene.
Synthesis of Polynitrodiazophenols
Atkins, Ronald L.,Wilson, William S.
, p. 2572 - 2578 (2007/10/02)
The formation of diazophenols by nitration of suitably substituted anilines and rearrangement of the nitroaromatic nitramines so formed is presented.The scope of the reaction is discussed, and a mechanism for the nitramine/diazophenol rearrangement is proposed which is consistent with 15N-labeling experiments.
Synthesis of Polynitrobenzenes. Oxidation of Polynitroanilines and Their N-Hydroxy, N-Methoxy, and N-Acetyl Derivatives
Atkins, Ronald L.,Nielsen, Arnold T.,Bergens, Cynthia,Wilson, William S.
, p. 503 - 507 (2007/10/02)
Nitro-substituted arylhydroxylamines and alkyloxyamines have been oxidized to polynitroaryl compounds by utilizing ozone.Polynitroanilines have been oxidized to polynitroaromatics by peroxydisulfuric acid generated in situ from SO3 and ozone.Thus N-hydroxy-2,4,6-trinitroaniline (1a) or N-methoxy-2,4,6-trinitroaniline (1b) was cleanly oxidized to 1,2,3,5-tetranitrobenzene (2) by reaction with ozone in methylene chloride.Weakly basic amines such as pentanitroaniline (10) can conveniently be oxidized to hexanitrobenzene (11) in high yields by simply dissolving the amine in oleum and introducing ozone.A variety of substituted arylamines have been oxidized to polynitroaromatic compounds by using these two oxidation techniques.
New method for preparing pentanitroaniline and triaminotrinitrobenzenes from trinitrotoluene
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, (2008/06/13)
Trinitrotoluene is selectively reduced by reaction with H2 S in p-dine to produce 4-amino-2,6-dinitrotoluene. This latter compound is then nitrated with HNO3 in H2 SO4 to produce pentanitroaniline which is, in
Synthesis of Polynitro Compounds. Peroxydisulfuric Acid Oxidation of Polynitroarylamines to Polynitro Aromatics.
Nielsen, Arnold T.,Atkins, Ronald L.,Norris, William P.,Coon, Clifford L.,Sitzmann, Michael E.
, p. 2341 - 2347 (2007/10/02)
Peroxydisulfuric acid in sulfuric acid solution, prepared by reaction of hydrogen peroxide with excess oleum or 100percent H2SO4, oxidizes primary polynitroarylamines and their N-acetamido derivatives to polynitro aromatics in good to excellent yields.The new procedure is illustrated by the synthesis of several new polynitro compounds, not preparable by known synthetic methods.Peroxytrifluoromethanesulfonic acid is comparably efficient for such oxidations.The scope and limitations of the new reaction have been examined and compared to other methods of synthesis of polynitro compounds.
