85166-83-2

Basic information

• Product Name: [Phenyl-(2,2,2-trifluoro-ethoxy)-methyl]-phosphonic acid diethyl ester
• Synonyms: [Phenyl-(2,2,2-trifluoro-ethoxy)-methyl]-phosphonic acid diethyl ester
• CAS NO: 85166-83-2
• Molecular Weight: 326.252
• Mol File: 85166-83-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [Phenyl-(2,2,2-trifluoro-ethoxy)-methyl]-phosphonic acid diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [Phenyl-(2,2,2-trifluoro-ethoxy)-methyl]-phosphonic acid diethyl ester(85166-83-2)
• EPA Substance Registry System: [Phenyl-(2,2,2-trifluoro-ethoxy)-methyl]-phosphonic acid diethyl ester(85166-83-2)

Safety Data

• Hazardous Substances Data: 85166-83-2(Hazardous Substances Data)

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 51761-45-6 Methanesulfonic acid (diethoxy-phosphoryl)-phenyl-methyl ester 

Relevant articles and documents

Mesylate Derivatives of α-Hydroxy Phosphonates. Formation of Carbocations Adjacent to the Diethyl Phosphonate Group

Mesylates 3-6 have been prepared and reacted in a variety of solvents.Product, rate, and solvent effect studies implicate carbocationic intermediates in these solvolyses despite the electron-withdrawing PO(OEt)2 group.Mesylate 3 gave exclusive substitution products.Optically active 3 gave racemic products on trifluoroacetolysis. α-Deuterium isotope effects were also in line with a cationic intermediate.Mesylate 4 gave some elimination product, 27, along with the substitution product 28, also via a cationic intermediate.Mesylates 5 and 6 gave exclusive elimination products.A β-deuterium isotope effect study gave a kH6/kD6 value of 2.8.This isotope effect, along with a small m value (0.45), suggested the intermediacy of a reversibly formed ion pair which subsequently loses a proton.This mechanism represents the merging of the classical E1 mechanism and the E2C(+) mechanism, the latter representing the cationic counterpart of the E1cb mechanism.Analysis of the solvolysis rates of 3 and 4 led to the conclusion that cationic intermediates are formed quite easily.Reasons are suggested for this unexpectedly facile generation of cations adjacent to the potent electron-withdrawing PO(OEt)2 substituent.