728-40-5Relevant articles and documents
Facile synthesis and physical and spectral characterization of 2,6-di-tert-butyl-4-nitrophenol (DBNP): a potentially powerful uncoupler of oxidative phosphorylation
Rivera-Nevares, Jose A.,Wyman, John F.,Minden, David L. von,Lacy, Nathan,Chabinyc, Michael L.,et al.
, p. 251 - 256 (1995)
The compound 2,6-di-tert-butyl-4-nitrophenol (DBNP), a potentially powerful uncoupler of ATP-generating oxidative phosphorylation, has been physically and spectroscopically characterized using X-ray crystallography, differential scanning calorimetry (DSC), thermal gravimetric analysis (TGA), GC-MS spectrometry, Fourier-transformed IR (FTIR) spectrophotometry, UV-VIS spectrophotometry, and FT (1)H- and (13)C-NMR spectroscopy. However, DBNP is not commercially available; therefore, it had to be synthesized in the laboratory prior to toxicity studies. The DBNP was prepared from 2,6-di-tert-butylphenol (DBP) precursor in hexane through an electrophilic aromatic substitution process using NO2. A collective yield of 75 percent was obtained by using two empirically determined end points that prevented the coprecipitation of reaction by-products and resulted in the formation of DBNP in high purity. Excessive amounts of NO2 in reaction mixtures resulted in the decomposition of preformed DBNP. With a pKa value of 6.8 and a higher degree of lipophilicity, DBNP may prove to be a stronger uncoupler of oxidative phosphorylation than 2,4-dinitrophenol (pKa=4.09) due to the expected enhancement of passive-diffusion kinetics across biological membranes at the physiological pH of 7.4. The present study is intended to provide analytical toxicologists, industrial hygiene monitors, and other professionals involved in chemical health and safety with a comprehensive source of basic information on the synthesis and analytical chemistry of DBNP.
Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Br?nsted Acidic NO2+ Generation
Juárez-Ornelas, Kevin A.,Jiménez-Halla, J. Oscar C.,Kato, Terumasa,Solorio-Alvarado, César R.,Maruoka, Keiji
supporting information, p. 1315 - 1319 (2019/03/07)
The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Br?nsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.
Chemoselective nitration of phenols with iert-butyl nitrite in solution and on solid support
Koley, Dlpankar,Colon, Olvia C.,Savlnov, Sergey N.
supporting information; experimental part, p. 4172 - 4175 (2009/12/30)
test-Butyl nitrite was identified as a safe and chemoselective nitrating agent that provides preferentially mononltro derivatives of phenolic substrates In the presence of potentially competitive functional groups. On the basis of our control experiments, we propose that the reaction proceeds through the formation of O-nltrosyl Intermediates prior to C-nitration via homolysis and oxidation. The reported nitration method Is compatible with tyroslne-containlng peptides on solid support In the synthesis of fluorogenic substrates for characterization of proteases.
