937-40-6Relevant articles and documents
Nitromethane with IBX/TBAF as a nitrosating agent: Synthesis of nitrosamines from secondary or tertiary amines under mild conditions
Potturi, Hima K.,Gurung, Ras K.,Hou, Yuqing
experimental part, p. 626 - 631 (2012/02/16)
Aliphatic or aromatic N,N-disubstituted nitrosamine was generated in fair to excellent yield from the reaction of a secondary or tertiary amine with o-iodoxybenzoic acid (IBX) or o-iodosylbenzoic acid (IBA)/R4NX (X = halide) and nitromethane. The product yield was strongly influenced by both the halide of R4NX and iodanes. IBX gave a higher yield than IBA, while the halides follow F- > Cl- > Br- ～ I-. Nitrous acid formed in situ from nitromethane and IBX (or IBA)/halides is likely responsible for the observed reaction.
Formation of N-nitrosamines and N-nitramines by the reaction of secondary amines peroxynitrite and other reactive nitrogen species: Comparison with nitrotyrosine formation
Masuda, Mitsuharu,Mower, Howard F.,Pignatelli, Brigitte,Celan, Irena,Friesen, Marlin D.,Nishino, Hoyoku,Ohshima, Hiroshi
, p. 301 - 308 (2007/10/03)
Reactive nitrogen species, including nitrogen oxides (N2O3 and N2O4), peroxynitrite (ONOO-), and nitryl chloride (NO2Cl), have been implicated as causes of inflammation and cancer. We studied reactions of secondary amines with peroxynitrite and found that both N-nitrosamines and N- nitramines were formed. Morpholine was more easily nitrosated by peroxynitrite at alkaline pH than at neutral pH, whereas its nitration by peroxynitrite was optimal at pH 8.5. The yield of nitrosomorpholine in this reaction was 3 times higher than that of nitromorpholine at alkaline pH, whereas 2 times more nitromorpholine than nitrosomorpholine was formed at pH 2N·), which react with nitric oxide (·NO) or nitrogen dioxide (·NO2) to yield nitroso and nitro secondary amines, respectively. Reaction of morpholine with NO· and superoxide anion (O2·-), which were concomitantly produced from spermine NONOate and by the xanthine oxidase systems, respectively, also yielded nitromorpholine, but its yield was 2·- inhibited its formation. Reactions of morpholine with nitrite plus HOCl or nitrite plus H2O2, with or without addition of myeloperoxidase or horseradish peroxidase, also yielded nitration and nitrosation products, in yields that depended on the reactants. Tyrosine was nitrated easily by synthetic peroxynitrite, by NaNO2 plus H2O2 with myeloperoxidase, and by NaNO2 plus H2O2 under acidic conditions. Nitrated secondary amines, e.g., N-nitroproline, could be identified as specific markers for endogenous nitration mediated by reactive nitrogen species.
Pseudophase Approach to Reactivity in Microemulsions: Quantitative Explanation of the Kinetics of the Nitrosation of Amines by Alkyl Nitrides in AOT/Isooctane/Water Microemulsions
Garcia-Rio, L.,Leis, J. R.,Mejuto, J. C.
, p. 10981 - 10988 (2007/10/03)
The kinetics of the nitroso group transfer from 2-ethoxyethyl (EEN) and 2-bromoethyl (BEN) nitrit+e to the secondary amines piperazine (PIP), N-methylbenzylamine (NMBA), and morpholine (MOR) in bis(2-ethylhexyl) sulfosuccinate (AOT)/isooctane(iC8)/water microemulsions were determined.They are explained quantitatively in terms of a model in which the reagents are distributed among the aqueous, organic, and AOT film surfactant, with the aqueous pseudophase and the surfactant film as the losi of the reaction.
