4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. A yellow solid, it is one of three isomers of nitroaniline. It is an intermediate in the production of dyes, antioxidants, pharmaceuticals, gasoline, gum inhibitors, poultry medicines, and as a corrosion inhibitor.
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InChI=1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2 |
TYMLOMAKGOJONV-UHFFFAOYSA-N |
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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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bacterial xenobiotic metabolite
Any bacterial metabolite produced by metabolism of a xenobiotic compound in bacteria.
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View more via ChEBI Ontology
1-amino-4-nitrobenzene
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NIST Chemistry WebBook
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4-nitraniline
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NIST Chemistry WebBook
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4-Nitroaniline
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KEGG COMPOUND
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4-NITROANILINE
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PDBeChem
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4-nitroaniline
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UniProt
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4-Nitrobenzeneamine
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KEGG COMPOUND
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p-aminonitrobenzene
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NIST Chemistry WebBook
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p-nitraniline
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NIST Chemistry WebBook
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p-Nitroaniline
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KEGG COMPOUND
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p-nitrophenylamine
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NIST Chemistry WebBook
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100-01-6
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CAS Registry Number
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KEGG COMPOUND
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100-01-6
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CAS Registry Number
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ChemIDplus
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100-01-6
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CAS Registry Number
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NIST Chemistry WebBook
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27331
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Gmelin Registry Number
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Gmelin
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508690
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Reaxys Registry Number
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Reaxys
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Khan F, Vyas B, Pal D, Cameotra SS (2013) Aerobic degradation of N-methyl-4-nitroaniline (MNA) by Pseudomonas sp. strain FK357 isolated from soil. PloS one 8, e75046 [PubMed:24116023] [show Abstract] N-Methyl-4-nitroaniline (MNA) is used as an additive to lower the melting temperature of energetic materials in the synthesis of insensitive explosives. Although the biotransformation of MNA under anaerobic condition has been reported, its aerobic microbial degradation has not been documented yet. A soil microcosms study showed the efficient aerobic degradation of MNA by the inhabitant soil microorganisms. An aerobic bacterium, Pseudomonas sp. strain FK357, able to utilize MNA as the sole carbon, nitrogen, and energy source, was isolated from soil microcosms. HPLC and GC-MS analysis of the samples obtained from growth and resting cell studies showed the formation of 4-nitroaniline (4-NA), 4-aminophenol (4-AP), and 1, 2, 4-benzenetriol (BT) as major metabolic intermediates in the MNA degradation pathway. Enzymatic assay carried out on cell-free lysates of MNA grown cells confirmed N-demethylation reaction is the first step of MNA degradation with the formation of 4-NA and formaldehyde products. Flavin-dependent transformation of 4-NA to 4-AP in cell extracts demonstrated that the second step of MNA degradation is a monooxygenation. Furthermore, conversion of 4-AP to BT by MNA grown cells indicates the involvement of oxidative deamination (release of NH2 substituent) reaction in third step of MNA degradation. Subsequent degradation of BT occurs by the action of benzenetriol 1, 2-dioxygenase as reported for the degradation of 4-nitrophenol. This is the first report on aerobic degradation of MNA by a single bacterium along with elucidation of metabolic pathway. | Agudelo-Morales CE, Silva OF, Galian RE, Pérez-Prieto J (2012) Nitroanilines as quenchers of pyrene fluorescence. Chemphyschem : a European journal of chemical physics and physical chemistry 13, 4195-4201 [PubMed:23090935] [show Abstract] The quenching of pyrene and 1-methylpyrene fluorescence by nitroanilines (NAs), such as 2-, 3-, and 4-nitroaniline (2-NA, 3-NA, and 4-NA, respectively), 4-methyl-3-nitroaniline (4-M-3-NA), 2-methyl-4-nitroaniline (2-M-4-NA), and 4-methyl-3,5-dinitroaniline (4-M-3,5-DNA), are studied in toluene and 1,4-dioxane. Steady-state fluorescence data show the higher efficiency of the 4-NAs as quenchers and fit with a sphere-of-action model. This suggests a 4-NA tendency of being in close proximity to the fluorophore, which could be connected with their high polarity/hyperpolarizability. In addition, emission and excitation spectra evidence the formation of emissive pyrene-NA ground-state complexes in the case of the 4-NAs and, in a minor degree, in the 2-NA. Moreover, time-resolved fluorescence experiments show that increasing amounts of NA decrease the pyrene fluorescence lifetime to a degree that depends on the NA nature and is larger in the less viscous solvent (toluene). Although the NA absorption and the pyrene (Py) emission overlap, we found no evidence of dipole-dipole energy transfer from the pyrene singlet excited state ((1)Py) to the NAs; this could be due to the low NA concentration used in these experiments. Transient absorption spectra show that the formation of the pyrene triplet excited state ((3)Py) is barely affected by the presence of the NAs in spite of their efficiency in (1)Py quenching, suggesting the involvement of (1)Py-NA exciplexes which--after intersystem crossing--decay efficiently into (3)Py. |
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