2,4-DIFLUOROANILINE - CAS 76563-56-9
Catalog number: 76563-56-9
Category: Main Product
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1.High resolution NMR study of T1 magnetic relaxation dispersion. III. Influence of spin 1/2 hetero-nuclei on spin relaxation and polarization transfer among strongly coupled protons.
Korchak SE1, Ivanov KL, Pravdivtsev AN, Yurkovskaya AV, Kaptein R, Vieth HM. J Chem Phys. 2012 Sep 7;137(9):094503. doi: 10.1063/1.4746780.
Effects of spin-spin interactions on the nuclear magnetic relaxation dispersion (NMRD) of protons were studied in a situation where spin ½ hetero-nuclei are present in the molecule. As in earlier works [K. L. Ivanov, A. V. Yurkovskaya, and H.-M. Vieth, J. Chem. Phys. 129, 234513 (2008); S. E. Korchak, K. L. Ivanov, A. V. Yurkovskaya, and H.-M. Vieth, ibid. 133, 194502 (2010)], spin-spin interactions have a pronounced effect on the relaxivity tending to equalize the longitudinal relaxation times once the spins become strongly coupled at a sufficiently low magnetic field. In addition, we have found influence of (19)F nuclei on the proton NMRD, although in the whole field range, studied protons and fluorine spins were only weakly coupled. In particular, pronounced features in the proton NMRD were found; but each feature was predominantly observed only for particular spin states of the hetero-nuclei. The features are explained theoretically; it is shown that hetero-nuclei can affect the proton NMRD even in the limit of weak coupling when (i) protons are coupled strongly and (ii) have spin-spin interactions of different strengths with the hetero-nuclei.
2.Relationships between the regioselectivity of the hydroxylation of C4-substituted 2-fluoroaniline derivatives and their toxic endpoints.
Cnubben NH1, van den Berg CL, Rietjens IM. Toxicol Appl Pharmacol. 1996 Dec;141(2):403-15.
The in vitro and in vivo metabolic profiles of a series of C4-substituted 2-fluoroanilines were determined and compared to their capacity to induce methemoglobinemia and nephrotoxicity in male Wistar rats. Qualitative and quantitative relationships between the biotransformation and the toxic endpoint of the halogenated anilines were defined. The rate of in vitro N-hydroxylation of the aniline derivatives correlated with the capacity of the compounds to induce methemoglobinemia (r = 0.96). In the experiments on the nephrotoxicity, attention was focused on the relative importance of the C4- and C6-hydroxylated metabolites of the C4-substituted 2-fluoroanilines. In vivo, the formation of 4-aminophenol metabolites was demonstrated to vary in the opposite order as the formation of the 6-aminophenol metabolites. 1H-NMR urinalysis and characterization of a set of conventional biochemical urinary parameters revealed the occurrence of nephrotoxicity upon exposure to the aniline derivatives and were most consistent with damage at the proximal tubular site.
3.Optimization of a novel series of N-phenylindoline-5-sulfonamide-based acyl CoA:monoacylglycerol acyltransferase-2 inhibitors: Mitigation of CYP3A4 time-dependent inhibition and phototoxic liabilities.
Sato K1, Takahagi H2, Kubo O2, Hidaka K2, Yoshikawa T2, Kamaura M2, Nakakariya M2, Amano N2, Adachi R2, Maki T2, Take K2, Takekawa S2, Kitazaki T2, Maekawa T2. Bioorg Med Chem. 2015 Aug 1;23(15):4544-60. doi: 10.1016/j.bmc.2015.06.003. Epub 2015 Jun 9.
Acyl CoA:monoacylglycerol acyltransferase-2 (MGAT2) has emerged as a potential peripheral target for the treatment of obesity and metabolic disorders. We previously identified a novel series of N-phenylindoline-5-sulfonamide derivatives exemplified by 2 as potent and orally bioavailable MGAT2 inhibitors. Despite its attractive potency, further assessment revealed that this compound exhibited time-dependent inhibition (TDI) of cytochrome P450 3A4 (CYP3A4). To remove the undesirable CYP3A4 TDI activity, structural modification was focused on the 2,4-difluoroaniline moiety on the basis of the assumption that this moiety would be involved in mechanism-based inhibition of CYP3A4 via oxidative metabolism. This led to the finding that the introduction of 4-chloro-2,6-difluoroaniline significantly improved CYP3A4 TDI risk. Further optimization resulted in the discovery of N-(4-chloro-2,6-difluorophenyl)-1-{5-[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]pyrimidin-2-yl}-7-(2-oxopyrrolidin-1-yl)-2,3-dihydro-1H-indole-5-sulfonamide (27c) with potent MGAT2 inhibitory activity (IC50=7.
4.Vibronic and cation spectroscopy of 2,4-difluoroaniline.
Huang WC1, Huang PS, Hu CH, Tzeng WB. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Jul;93:176-9. doi: 10.1016/j.saa.2012.03.015. Epub 2012 Mar 15.
We applied the two-color resonant two-photon ionization and mass-analyzed threshold ionization techniques to record the vibronic and cation spectra of 2,4-difluoroaniline. The cation spectra were recorded by ionizing via the 0(0), X(1), 6b(1), and 1(1) levels of the electronically excited S(1) state. Most of the observed active modes of this molecule in the S(1) and cationic ground D(0) states are related to the in-plane ring deformation vibrations. The band origin of the S(1)←S(0) electronic excitation was found to appear at 33294 ± 2 cm(-1), whereas the adiabatic ionization energy was determined to be 63935 ± 5 cm(-1). Comparing the data of 2,4-difluoroaniline with those of aniline, 2-fluoroaniline, and 4-fluoroaniline, one can learn the effects of fluorine substitution on the electronic transition and molecular vibration.
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