5213-50-3Relevant academic research and scientific papers
Study of the methylation reaction of 2,4-dinitroimidazole and potassium 2,4,5-trinitroimidazol-1-ide with dimethyl sulfate
Lian, Peng-Bao,Yuan, Yuan,Chen, Jian,Chen, Li-Zhen,Wang, Jian-Long
, p. 1010 - 1014 (2020/10/02)
[Figure not available: see fulltext.] The methylation of 2,4-dinitroimidazole and potassium salt of 2,4,5-trinitroimidazole with dimethyl sulfate was reinvestigated. When the reaction system contained a weak base, the reaction products were 1-methyl-2,4-dinitroimidazole and 1-methyl-2,4,5-trinitroimidazole, respectively. However, in the absence of a base in the reaction system, the products contained oxidation byproducts 1-methylimidazolidine-2,4,5-trione, 1,3-dimethylimidazolidine-2,4,5-trione and recovered starting materials. All products were characterized using FT-IR, NMR, and elemental analysis. The structure of 1-methylimidazolidine-2,4,5-trione and 1,3-dimethylimidazolidine-2,4,5-trione were further confirmed by single crystal X-ray diffraction.
Selective reduction of 2,4-dinitro- and 4,5-dinitroimidazole derivatives using iron dust
Olender, Dorota,Zwawiak, Justyna,Zaprutko, Lucjusz
scheme or table, p. 1049 - 1055 (2010/10/21)
(Chemical Equation Presented) A series of N-substituted 2,4-dinitroimidazoles, 4,5-dinitroimidazoles, and 2-methyl-4,5-dinitroimidazoles have been selectively reduced to the corresponding aminonitroimidazole derivatives, using iron dust in glacial acetic acid at room temperature. 2,4-Dinitroimidazoles have been reduced to the 2-amino-4-nitro-derivatives only but 4,5-dinitroimidazoles have given 4-amino-5-nitro- or 5-amino-4- nitroderivatives depended on the structure of the N-substituent.
Melt-cast explosive material
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Page/Page column 7, (2008/06/13)
1-Methyl-2,4,5-Trinitroimidazole is synthesized starting from 4-nitroimidazole using stepwise nitration method and further methylation using Dimethylsulphate. It is relatively insensitive to impact and its thermal stability is excellent. The calculated detonation properties indicate that its performance is about 30% better than TATB. It can be prepared easily, with reasonable yield, starting from commercially available Imidazole. Results from impact sensitivity, friction sensitivity, time-to-explosion temperature and vacuum stability tests indicate that it is less sensitive than both RDX and HMX. The good oxygen balance and measured heat of formation data of this material indicate that its propellant performance should be good.
Strategies toward the design of energetic ionic liquids: Nitro- and nitrile-substituted N,N′-dialkylimidazolium salts
Katritzky, Alan R.,Yang, Hongfang,Zhang, Dazhi,Kirichenko, Kostyantyn,Smiglak, Marcin,Holbrey, John D.,Reichert, W. Matthew,Rogers, Robin D.
, p. 349 - 358 (2007/10/03)
Twelve novel 1,3-dialkylimidazolium salts containing strongly electron-withdrawing nitro- and cyano-functionalities directly appended to the cationic heterocyclic rings have been synthesized; the influences of the substituents on both formation and thermal properties of the resultant ionic liquids have been determined by DSC, TGA, and single crystal X-ray diffraction, showing that an electron-withdrawing nitro-substituent can be successfully appended and has a similar influence on the melting behaviour as that of corresponding methyl group substitution. Synthesis of di-, or trinitro-substituted 1,3-dialkylimidazolium cations was unsuccessful due to the resistance of dinitro-substituted imidazoles to undergo either N-alkylation or protonation, while 1-alkyl-4,5-dicyanoimidazoles were successfully alkylated to obtain 1,3-dialkyl-4,5-dicyanoimidazolium salts. Five crystal structures (one of each cation type) show that, in the solid state, the NO2-group has little significant effect, beyond the steric contribution, on the crystal packing. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.
Nitroimidazoles: Part XI - Some Halonitro- and Dinitroimidazoles
Sudarsanam, V.,Nagarajan, K.,George, T.,Shenoy, S. J.,Iyer, V. V.,Kaulgud, A. P.
, p. 1022 - 1026 (2007/10/02)
Methylation of 2-chloro-4-nitroimidazole (6), obtained from imidazole in four steps, either with dimethyl sulphate or with diazomethane affords a mixture of 2-chloro-1-methyl-5-nitroimidazole (10) and the 4-nitro-isomer (7).The corresponding dinitro compounds 11 and 8 are formed in the methylation of 2,4-dinitroimidazole (5), 8 being converted to 7 by the action of POCl3.Reaction of 10 with the sodium salt of N-methanesulphonyl-2-imidazolidinone provides the potent amoebicide, 1-methylsulphonyl-3-(1-methyl-5-nitroimidazol-2-yl)-2-imidazolidinone (2).The isomer 14 issynthesised from 7 in low yield.Ethylation of 5 leads to preponderant N-alkylation, providing a mixture of 1-ethyl dinitroimidazoles (9) and (12), but a small amount of N,C-diethyl derivative 15 is also obtained.The formation of 15 from 5 is rationalised.The diiodination product of imidazole is shown to be 4,5-diiodoimidazole (19), nitric acid transforming it to 4-iodo-5-nitroimidazole (20).Methylation of 20 affords a mixture of isomeric 1-methyliodonitro derivatives (21) and (22).The structures of 21 and 22 are established by 13C NMR data as well as by conversion into morpholine derivatives 26 and 24 respectively which also arise from 1-methylchloronitroimidazoles (25) and (23).A mechanism is proposed for the reported conversion of 5 into 4-chloro-5-nitroimidazole (32) in boiling 2-chloroethanol.
NITROIMIDAZOLES. PART V. CHLORONITROIMIDAZOLES FROM DINITROIMIDAZOLES. A REINVESTIGATION
Suwinski, Jerzy,Salwinska, Ewa,Watras, Jan,Widel, Maria
, p. 1261 - 1272 (2007/10/02)
5(4)-Chloro-4(5)-nitroimidazole and 2-chloro-4(5)-nitroimidazole or their N-methyl derivatives have been synthesized in at least two independent routes.In contrast to some former reports it has been established that from 2,4(or 5)-dinitroimidazoles only 2-chloro-4(or 5)-nitroimidazoles are obtained.In 4,5-dinitroimidazoles only a nitro group in the 5-position is replaced by a chlorine atom.Structures of the obtained compounds have been confirmed by analyses of physico-chemical data.
