Lazarus, Robert A. published the artcileMechanism of hydrolysis of phosphorylethanolamine triesters. Multiple catalytic effects of an intramolecular amino group, Safety of 2-((2,2,2-Trifluoroethyl)amino)ethanol, the publication is Journal of the American Chemical Society (1979), 101(15), 4300-12, database is CAplus.
Intramol. displacement reactions at P are examined in N-alkyl-O-(arylphenylphosphoryl)ethanolamines in 45% dioxane-water (volume) at 35°. The examination of the pH-rate profiles, the detection of external buffer catalysis, and the observation of D solvent effects reveal the concurrent operation of 3 types of P-O bond cleavage mechanisms: electrostatic catalysis by the protonated ammonium moiety of external nucleophilic attack by buffer bases at D, general base-catalyzed intramol. nucleophilic attack by the amino function to form the cyclic phosphoramidate, and intramol. amine-assisted water displacement of the substituted phenol. A Broensted plot for the general base-catalyzed cyclization reaction supports either a concerted mechanism for the cyclization process bypassing the formation of a pentacovalent intermediate with a discrete lifetime or a mechanism involving H bonding stabilization of the rate-determining decomposition of the intermediate providing that this is faster than the diffusion away of the catalyst. In either case the lifetime of the pentacovalent intermediate is <10-12s.
Journal of the American Chemical Society published new progress about 371-99-3. 371-99-3 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is 2-((2,2,2-Trifluoroethyl)amino)ethanol, and the molecular formula is C4H8F3NO, Safety of 2-((2,2,2-Trifluoroethyl)amino)ethanol.
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