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75-87-6Relevant articles and documents
Synthesis, spectral properties, crystal structure and theoretical calculations of a new geminal diamine: 2,2,2-Trichloro-N,N?-bis(2-nitrophenyl)-ethane-1,1-diamine
Ayd?n, Fatma,Arslan, N Burcu
, (2021)
A new 2,2,2-trichloro-N,N?-bis(2-nitrophenyl)-ethane-1,1-diamine was synthesized by the reaction of 2-nitroaniline in DCM with the chloral formed by distillation of chloral hydrate over concentrated H2SO4. The structure of the title compound was identified by means of FT-IR, 1H NMR, and 13C NMR spectroscopic techniques. The crystal structure of the title compound has also been examined by using X-ray crystallographic techniques and found to be crystallized in the monoclinic crystal system and space group P21/n with the unit cell parameters: a = 7.7075(12) ?, b = 7.7396(10) ?, c = 28.247(4) ?, β = 93.602(5)°, V = 1681.7(4) ?3, Dx = 1.602 Mg m ? 3, and Z = 4 respectively. The calculated electronic structure properties of the title molecule such as HOMO-LUMO analysis, molecular electrostatic potential (MEP) map, and the Mulliken charge distributions were investigated by using the density functional theory (DFT) method. Theoretically calculated values exhibit the chemically hard, high kinetic stable and less reactive molecule.
Substituted nitrogen-bridged diazocines
Griebenow, Thomas,Herges, Rainer,Lentes, Pascal,Rudtke, Jeremy
supporting information, p. 1503 - 1508 (2021/07/02)
Novel nitrogen-bridged diazocines (triazocines) were synthesized that carry a formyl or an acetyl group at the CH2NR-bridge and bromo- or iodo-substituents at the distant phenyl ring. The photophysical properties were investigated in acetonitrile and water. As compared to previous approaches the yields of the intramolecular azo cyclizations were increased (from ≈40 to 60%) using an oxidative approach starting from the corresponding aniline precursors. The Z→E photoconversion yields in acetonitrile are 80–85% and the thermal half-lives of the metastable E configurations are 31–74 min. Particularly, the high photoconversion yields (≈70%) of the water-soluble diazocines are noteworthy, which makes them promising candidates for applications in photopharmacology. The halogen substituents allow further functionalization via cross-coupling reactions.
Photocatalytic degradation of gaseous trichloroethylene on porous titanium dioxide pellets modified with copper(II) under visible light irradiation
Tashiro, Keigo,Tanimura, Toshifumi,Yamazaki, Suzuko
, p. 228 - 235 (2019/04/17)
Porous titanium dioxide pellets modified with copper(II) ion (Cu-TiO2) were synthesized by sol-gel method with dialysis for photocatalytic degradation of gaseous trichloroethylene (TCE) under visible light (VL) irradiation. TCE was completely degraded by passing the gas stream (mole fractions of oxygen and TCE were 0.2 and 1.75 × 10?4, respectively) at the flow rate of 25 mL min?1 through 0.2 g of the Cu-TiO2 pellets (Cu content: 0.1 atom%) calcined at 200 °C. TCE was converted mainly to carbon dioxide, dichloroacetic acid (DCAA), and inorganic chlorine species. Relatively small quantities of pentachloroethane (PCA) and trichloroacetaldehyde (TCAH) were detected as products on the Cu-TiO2 surface. Comparison with porous TiO2 pellets under ultraviolet irradiation revealed that more chlorinated products and less carbon dioxide were formed on Cu-TiO2 under VL irradiation. The mineralization of TCE to carbon dioxide was calculated to be only ca. 30.0%. It is noted that DCAA, PCA and TCAH were accumulated on the surface and were extracted with ethyl acetate. The porous Cu-TiO2 pellets show promise as the photocatalyst acting under VL irradiation for converting TCE gas to chlorinated compounds which can be used in industries.
Ciprofloxacin degradation in UV/chlorine advanced oxidation process: Influencing factors, mechanisms and degradation pathways
Deng, Jia,Wu, Guangxue,Yuan, Shoujun,Zhan, Xinmin,Wang, Wei,Hu, Zhen-Hu
, p. 151 - 158 (2018/11/24)
Ciprofloxacin (CIP) is a widely used third generation fluoroquinolone antibiotics, and has been often detected in wastewater treatment plants. Finding an effective way to remove them from wastewater is of great concern. Ultraviolet (UV)/chlorine advanced oxidation process (AOP) has many advantages in micropollutant removal. In this study, CIP degradation in UV/chlorine process was investigated. Only 41.2% of CIP was degraded by UV photolysis and 30.5% by dark chlorination in 30 min, while 98.5% of CIP was degraded by UV/chlorine process in 9 min. HCO3 ? had markedly inhibition, NO3 ? and SO4 2- had slight inhibition, and Cl? had a marginal inhibition on CIP degradation in UV/chlorine system. The degradation of CIP in UV/chlorine process was mainly attributed to the attack of reactive species. The relative contributions of hydrated electrons (eaq [rad]), hydroxyl radicals (HO[rad]), chlorine atoms (Cl[rad]), and UV photolysis were investigated. Under neutral condition in aqueous solution, CIP degradation had highest pseudo first-order reaction rate constant, in which eaq [rad] had the highest contribution, followed by Cl[rad], HO[rad], and UV photolysis. The intermediates and byproducts were identified and the degradation pathway was proposed. The total organic chlorine (TOCl) and biotoxicity were further assessed. CIP and natural organic matters (NOMs) were removed efficiently in real water. UV/chlorine showed the potential for the wastewater treatment containing CIP.
Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics
Wünsch, Matthias,Schr?der, David,Fr?hr, Tanja,Teichmann, Lisa,Hedwig, Sebastian,Janson, Nils,Belu, Clara,Simon, Jasmin,Heidemeyer, Shari,Holtkamp, Philipp,Rudlof, Jens,Klemme, Lennard,Hinzmann, Alessa,Neumann, Beate,Stammler, Hans-Georg,Sewald, Norbert
supporting information, p. 2428 - 2441 (2017/12/06)
The amide moiety of peptides can be replaced for example by a triazole moiety, which is considered to be bioisosteric. Therefore, the carbonyl moiety of an amino acid has to be replaced by an alkyne in order to provide a precursor of such peptidomimetics. As most amino acids have a chiral center at Cα, such amide bond surrogates need a chiral moiety. Here the asymmetric synthesis of a set of 24 N-sulfinyl propargylamines is presented. The condensation of various aldehydes with Ellman's chiral sulfinamide provides chiral N-sulfinylimines, which were reacted with (trimethylsilyl)ethynyllithium to afford diastereomerically pure N-sulfinyl propargylamines. Diverse functional groups present in the propargylic position resemble the side chain present at the Cα of amino acids. Whereas propargylamines with (cyclo)alkyl substituents can be prepared in a direct manner, residues with polar functional groups require suitable protective groups. The presence of particular functional groups in the side chain in some cases leads to remarkable side reactions of the alkyne moiety. Thus, electron-withdrawing substituents in the Cα-position facilitate a base induced rearrangement to α,β-unsaturated imines, while azide-substituted propargylamines form triazoles under surprisingly mild conditions. A panel of propargylamines bearing fluoro or chloro substituents, polar functional groups, or basic and acidic functional groups is accessible for the use as precursors of peptidomimetics.
Liebeskind-Srogl cross-coupling on γ-carboxyl-γ-butyrolactone derivatives: Application to the side chain of amphidinolides C and F
Fenneteau, Johan,Vallerotto, Sara,Ferrié, Laurent,Figadère, Bruno
supporting information, p. 3758 - 3761 (2015/06/08)
The synthetic approach for the C20-C29 and C20-C34 fragments of amphidinolide F and C was based on an original Liebeskind-Srogl cross-coupling reaction with a glutamic acid-derived building-block. Further highly diastereoselective reduction of the ketone was achieved by using an uncommon Ph3SiH/TBAF/HMPA system. The amphidinolide C side chain was built through a reductive elimination of chiral epoxide to install the stereogenic center at C29.
Facile stereoselective synthesis of 1,3-disubstituted-4-trichloromethyl azetidin-2-ones
Govande,Deshmukh
, p. 6563 - 6566 (2007/10/03)
The highly stereoselective synthesis of 1,3-disubstituted-4-trichloromethyl azetidin-2-ones by the [2+2] cycloaddition of ketenes with imines derived from chloral is described. The highly stereoselective synthesis of 1,3-disubstituted-4-trichloromethyl azetidin-2-ones by the [2+2] cycloaddition of ketenes with imines derived from chloral is described.
METHOD OF MAKING HYDROFLUOROCARBONS
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Page 17, (2008/06/13)
A method of producing hydrofluorocarbons and methods of producing other commercially attractive compounds formed as by-products of hydrofluorocarbon production by using aldehydes as a principal reactant.
Degradation pathways of trichloroethylene and 1,1,1-trichloroethane by Mycobacterium sp. TA27
Hashimoto, Akiko,Iwasaki, Kazuhiro,Nakasugi, Naou,Nakajima, Mutsuyasu,Yagi, Osami
, p. 385 - 390 (2007/10/03)
We analyzed the kinetics and metabolic pathways of trichloroethylene and 1,1,1-trichloroethane degradation by the ethane-utilizing Mycobacterium sp. TA27. The apparent Vmax and Km of trichloroethylene were 9.8 nmol min-1 m
Microsomal oxidation of tribromoethylene and reactions of tribromoethylene oxide.
Yoshioka, Tadao,Krauser, Joel A,Guengerich, F Peter
, p. 1414 - 1420 (2007/10/03)
Halogenated olefins are of interest because of their widespread use in industry and their potential toxicity to humans. Epoxides are among the enzymatic oxidation products and have been studied in regard to their toxicity. Most of the attention has been given to chlorinated epoxides, and we have previously studied the reactions of the mono-, di-, tri-, and tetrachloroethylene oxides. To further test some hypotheses concerning the reactivity of these compounds, we prepared tribromoethylene (TBE) oxide and compared it to trichloroethylene (TCE) oxide and other chlorinated epoxides. TBE oxide reacted with H(2)O about 3 times faster than did TCE oxide. Several hydrolysis products of TBE oxide were the same as formed from TCE oxide, i.e., glyoxylic acid, CO, and HCO(2)H. Br(2)CHCO(2)H was formed from TBE oxide; the yield was higher than for Cl(2)CHCO(2)H formed in the hydrolysis of TCE oxide. The yield of tribromoacetaldehyde was 0.4% in aqueous buffer (pH 7.4). In rat liver microsomal incubations containing TBE and NADPH, Br(2)CHCO(2)H was a major product, and tribromoacetaldehyde was a minor product. These results are consistent with schemes previously developed for halogenated epoxides, with migration of bromine being more favorable than for chlorine. Reaction of TBE oxide with lysine yielded relatively more N-dihaloacetyllysine and less N-formyllysine than in the case of TCE oxide. This same pattern was observed in the products of the reaction of TBE oxide with the lysine residues in bovine serum albumin. We conclude that the proposed scheme of hydrolysis of halogenated epoxides follows the expected halide order and that this can be used to rationalize patterns of hydrolysis and reactivity of other halogenated epoxides.