1‐Fluoro‐2,4,6‐trimethylpyridinium Trifluoromethanesulfonate

[1007264-00-6] C9H11F4NO3S (MW 289.25) InChI = 1S/C8H11FN.CHF3O3S/c1-6-4-7(2)10(9)8(3)5-6;2-1(3,4)8(5,6)7/h4-5H,1-3H3;(H,5,6,7)/q+1;/p-1 InChIKey = PRIGFEJKMMRJSF-UHFFFAOYSA-M (electrophilic fluorinating reagent) Alternate Name: 1-fluoro-2,4,6-trimethylpyridinium triflate. Physical Data: mp 162 °C; stable crystals that remained intact after 5 h at 150 °C but melted and decomposed within a few minutes at 190 °C. Solubility: soluble in polar solvents such as CH3CN and even in water without decomposition after 30 days at room temperature, but insoluble or hardly soluble in nonpolar organic solvents. Form Supplied in: commercially available as a light yellow solid. Preparative Methods: 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate can be prepared by fluorination of the corresponding pyridine with molecular fluorine (diluted in nitrogen) at low temperature in the presence of metal triflate salts (sodium, potassium, or lithium).1-3 Purification: recrystallization from CH3CN–diethyl ether at room temperature. Handling, Storage, and Precautions: irritant; handle with caution and minimize exposure. This compound must be stored in a cool and shaded area. Keep away from heat and oxidizing agents.

[1]  T. Mei,et al.  Versatile Pd(OTf)2 x 2 H2O-catalyzed ortho-fluorination using NMP as a promoter. , 2009, Journal of the American Chemical Society.

[2]  Shoko Suzuki,et al.  Asymmetric fluorination of β-keto esters catalyzed by chiral rare earth perfluorinated organophosphates , 2006 .

[3]  Y. Kondo,et al.  1-Fluoropyridinium triflates: versatile reagents for transformation of thioglycoside into O-glycoside, glycosyl azide and sulfoxide , 2003 .

[4]  Susumu Sato,et al.  α, α-gem-Difluorination of α-(Alkylthio)acetophenone Derivatives with N-Fluoropyridinium Salts , 2000 .

[5]  S. Ivanov,et al.  Fluorination of deltahedral closo-borane and -carborane anions with N-fluoro reagents , 1998 .

[6]  J. Ortiz,et al.  7-[3-(1-piperidinyl)propoxy]chromenones as potential atypical antipsychotics. , 1996, Journal of medicinal chemistry.

[7]  H. Toda,et al.  Synthesis and Properties of Fluoroazulenes. II. Electrophilic Fluorination of Azulenes with N-Fluoro Reagents , 1996 .

[8]  T. Fuchigami,et al.  Electrolytic partial fluorination of organic compounds. Part 15. Stereochemical study of the anodic monofluorination of α-phenylsulfenyl acetates , 1995 .

[9]  H. Toda,et al.  THE FIRST SYNTHESIS OF 1-FLUORO- AND 1,3-DIFLUOROAZULENES , 1995 .

[10]  A. Kiselyov.  Reaction of N-fluoropyridinium salts with wittig reagents: A novel and convenient approach to symmetric trans-olefins , 1994 .

[11]  I. Shimizu,et al.  Synthesis of α-fluoroketones based on palladium-catalyzed Decar☐ylation reactions of allyl β-keto car☐ylates , 1994 .

[12]  L. Strekowski,,et al.  Efficient hydrolysis of dithioacetals by the N-fluoro-2,4,6-trimethylpyridinium triflate-water system , 1993 .

[13]  M. Ihara,et al.  Enantioselective construction of quaternary stereogenic centres possessing a fluorine atom , 1992 .

[14]  T. Umemoto,et al.  Syntheses and properties of N-fluoropyridinium salts , 1991 .

[15]  T. Umemoto,et al.  Power and Structure-Variable Fluorinating Agents. The N- Fluoropyridinium Salt System. , 1990 .

[16]  M. Ihara,et al.  Enantioselective synthesis of monofluorinated chiral building blocks from malonic acid , 1990 .

[17]  A. W. Czarnik,et al.  Structural effects controlling the rate of the retro-Diels-Alder reaction in anthracene cycloadducts , 1989 .

[18]  T. Umemoto,et al.  α-Fluorination of Sulfides with N-Fluoropyridinium Triflates , 1986 .

[19]  T. Umemoto,et al.  N-fluoropyridinium triflate and its derivatives: useful fluorinating agents , 1986 .

[20]  T. Umemoto,et al.  N-Fluoropyridinium triflate and its analogs, the first stable 1:1 salts of pyridine nucleus and halogen atom , 1986 .