ChemInform Abstract: DIRECT NITRATION OF BENZIMIDAZOLONE AND REDUCTION OF SOME OF THE NITRATION PRODUCTS

Schindlbauer, H.; Kwiecinski, Wlodzimierz

doi:10.1002/chin.197726238

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“…m.p. 313–315 °C (dec.) [ 32 ]. The obtained reaction product (TriNBO) was pure and did not contain any impurities of dinitro- or tetranitro-derivatives (LC-MS analysis data are presented below in the next section in Figure 2 a,b).…”

Section: Methodsmentioning

confidence: 99%

An Efficient Synthesis and Preliminary Investigation of Novel 1,3-Dihydro-2H-benzimidazol-2-one Nitro and Nitramino Derivatives

2022

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The preparation and properties of a series of novel 1,3-dihydro-2H-benzimidazol-2-one nitro and nitramino derivatives are described. A detailed crystal structure of one of the obtained compounds, 4,5,6-trinitro-1,3-dihydro-2H-benzimidazol-2-one (TriNBO), was characterized using low temperature single crystal X-ray diffraction, namely an orthorhombic yellow prism, space group ‘P 2 21 21’, experimental crystal density 1.767 g/cm3 (at 173K). Methyl analog, 5-Me-TriNBO-monoclinic red plates, space group, P 21/c, crystal density 1.82 g/cm3. TriNBO contains one activated nitro group at the fifth position, which was used for the nucleophilic substitution in the aminolysis reactions with three monoalkylamines (R=CH3, C2H5, (CH2)2CH3) and ethanolamine. The 5-R-aminoderivatives were further nitrated with N2O5/ HNO3 and resulted in a new group of appropriate nitramines: 1,3-dihydro-2H-5-R-N(NO2)-4,7-dinitrobenzimidazol-2-ones. Thermal analysis (TGA) of three selected representatives was performed. The new compounds possess a high melting point (200–315 °C) and thermal stability and can find a potential application as new thermostable energetic materials. Some calculated preliminary energetic characteristics show that TriNBO, 5-Me-TriNBO, 5-methylnitramino-1,3-dihydro-2H-4,7-dinitrobenzimidazol-2-one, and 5-nitratoethylnitramino-1,3-dihydro-2H-4,7-dinitrobenzimidazol-2-one possess increased energetic characteristics in comparison with TNT and tetryl. The proposed nitrocompounds may find potential applications as thermostable high-energy materials.

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Section: Methodsmentioning

confidence: 99%

An Efficient Synthesis and Preliminary Investigation of Novel 1,3-Dihydro-2H-benzimidazol-2-one Nitro and Nitramino Derivatives

2022

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ChemInform Abstract: DIRECT NITRATION OF BENZIMIDAZOLONE AND REDUCTION OF SOME OF THE NITRATION PRODUCTS

Abstract: Die Nitrierung der Titelverbindung (II) zum Mono‐ (Ia), Di‐[(Ib) bzw. ‐ (III)‐analoges Tautomeres], Tri‐ (IIIa) bzw. Tetranitroderivat (IIIb) gelingt mit konz. bzw. rauchender HNO3 unter den angegebenen Bedingungen.

Cited by 1 publication

References 1 publication

An Efficient Synthesis and Preliminary Investigation of Novel 1,3-Dihydro-2H-benzimidazol-2-one Nitro and Nitramino Derivatives

An Efficient Synthesis and Preliminary Investigation of Novel 1,3-Dihydro-2H-benzimidazol-2-one Nitro and Nitramino Derivatives

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