Abstract
In the title compound, C10H11N3O6, the torsion angles about the bonds to the benzene ring are less than 4°, except for the nitro groups, which are twisted out of the ring plane by 25.27 (3) and 43.63 (2)°. The N-H group forms a bifurcated hydrogen bond, with an intra-molecular component to a nitro group O atom and an inter-molecular component to the other nitro group, thereby forming chains propagating in the [010] direction. Several weak C-H⋯O inter-actions are also present.
Highlights
In the title compound, C10H11N3O6, the torsion angles about the bonds to the benzene ring are less than 4, except for the nitro groups, which are twisted out of the ring plane by 25.27 (3) and 43.63 (2)
The N—H group forms a bifurcated hydrogen bond, with an intramolecular component to a nitro group O atom and an intermolecular component to the other nitro group, thereby forming chains propagating in the [010] direction
We believe that 4-AcP, like its putative major metabolite, 4-acetamidophenol (4-AP) (Hinson, 1983; Lakshmi et al, 2000; Liu et al, 2019), undergoes oxidative transformation by cellular oxidants such as hypochlorite/ hypochlorous acid and peroxynitrite/peroxynitrous acid and forms chlorinated and nitrated products. Towards understanding this and to shed light on molecular targets, we have synthesized the title compound 2,5-dinitro-4-AcP, C10H11N3O6, and we report its structure
Summary
The analgesic use of 4-acetamidophenetole (4-AcP) predates the First World War. 4-AcP was likely the first synthetic chemical to go on the market as a fever reducer, but was withdrawn from global markets three decades ago due to its carcinogenic and kidneydamaging properties (Zeman, 1963; Carrociampi, 1978; Leistenschneider et al, 1983; Holmang et al, 2013). We believe that 4-AcP, like its putative major metabolite, 4-acetamidophenol (4-AP) (Hinson, 1983; Lakshmi et al, 2000; Liu et al, 2019), undergoes oxidative transformation by cellular oxidants such as hypochlorite/ hypochlorous acid and peroxynitrite/peroxynitrous acid and forms chlorinated and nitrated products. Towards understanding this and to shed light on molecular targets, we have synthesized the title compound 2,5-dinitro-4-AcP, C10H11N3O6, and we report its structure.
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