107264-00-6

Basic information

• Product Name: 1-FLUORO-2,4,6-TRIMETHYLPYRIDINIUM TRIFLATE
• Synonyms: N-Fluoro-2,4,6-trimethylpyridinium triflate,85-90%;Florinate FP-T 300;FP-T 300;Onoda Florinate FP-T 300;N-Fluoro-2,4,6-trimethylpyridinium triflate, N-Fluoro-2,4,6-collidinium triflate;N-Fluoro-2,4,6-trimethylpyridinium trifluoromethanesulphonate 97%;N-Fluoro-2,4,6-trimethylpyridiniumtrifluoromethanesulphonate97%;N-FLUORO-2,4,6-TRIMETHYLPYRIDINIUM TRIFLATE
• CAS NO: 107264-00-6
• Molecular Formula: CF₃O₃S*C₈H₁₁FN
• Molecular Weight: 289.25
• Product Categories: Pyridinium Compounds;Synthetic Organic Chemistry;Electrophilic Fluorinating Reagents;Fluorinating Reagents;Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds;Fluorination;Halogenation
• Mol File: 107264-00-6.mol

Chemical Properties

• Melting Point: 162-165 °C(lit.)
• Appearance: white to pale-yellow/Powder
• Density: 1.3855 (estimate)
• Storage Temp.: 0-6°C
• Sensitive: air sensitive, moisture sensitiv
• BRN: 4777118
• CAS DataBase Reference: 1-FLUORO-2,4,6-TRIMETHYLPYRIDINIUM TRIFLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-FLUORO-2,4,6-TRIMETHYLPYRIDINIUM TRIFLATE(107264-00-6)
• EPA Substance Registry System: 1-FLUORO-2,4,6-TRIMETHYLPYRIDINIUM TRIFLATE(107264-00-6)

Safety Data

• Hazard Codes: Xi,C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45-36
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• TSCA: No
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 107264-00-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1-FLUORO-2,4,6-TRIMETHYLPYRIDINIUM TRIFLATE is used as a reactant for Pd(II)-catalyzed para-selective C-H arylation, enabling the selective formation of desired products in the presence of a palladium catalyst.
Used in Fluorination Reactions:
1-FLUORO-2,4,6-TRIMETHYLPYRIDINIUM TRIFLATE is utilized as a reactant in fluorination reactions, where it aids in the introduction of a fluorine atom into a molecule, which is crucial for various pharmaceutical and chemical applications.
Used in Oxidative Processes:
1-FLUORO-2,4,6-TRIMETHYLPYRIDINIUM TRIFLATE acts as an oxidant in oxidatively-induced aryl-CF3 bond-formation, promoting the formation of aryl-trifluoromethyl (aryl-CF3) bonds, which are important in the synthesis of various organic compounds.
Used in Pd(II)-catalyzed C-H Olefination Reactions:
The compound is employed as a reactant in Pd(II)-catalyzed C-H olefination reactions, where it facilitates the formation of olefins from alkanes through the C-H activation process, which is a significant step in the synthesis of complex organic molecules.

InChI:InChI=1/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

Upstream product

• 108-75-8 2,4,6-trimethyl-pyridine 
• 2926-27-4 potassium trifluoromethansulfonate 
• 2926-30-9 sodium triflate 
• 33454-82-9 lithium trifluoromethanesulfonate 
• 2926-29-6 Langlois reagent 

Downstream Products

• 2924-74-5 fluoromethyl benzyl sulfide 
• 60839-94-3 2-fluoro-methylthiobenzene 
• 65325-65-7 1-chloro-4-[(fluoromethyl)sulfanyl]benzene 
• 1239698-98-6 trans-[(FC₆H₄C₆H₃CH₂P(1-adamantyl)2)Pt(triphenylphosphine)(pyridine)]triflate 
• 1215465-52-3 (4,4'-di-tert-butyl-2,2'-bipyridine)Pd(IV)F(p-FC₆H₄)(CF₃)(OTf) 
• 1346257-61-1 [(fac-1,1-bis(2-pyridyl)phenylethane(-1H))Pd(4-nitrophenolato)(4-MeC₆H₄)(trifluoromethyl)] 
• 1346257-60-0 [(fac-1,1-bis(2-pyridyl)phenylethane(-1H))Pd(PMe₃)(4-MeC₆H₄)(trifluoromethyl)]OTf 
• 1346257-58-6 [(fac-1,1-bis(2-pyridyl)phenylethane(-1H))Pd(tert-butyl isocyanide)(4-MeC₆H₄)(trifluoromethyl)]OTf 
• 1346257-56-4 [(fac-1,1-bis(2-pyridyl)phenylethane(-1H))PdCl(4-MeC₆H₄)(trifluoromethyl)] 
• 1729-20-0 5-methyl-3,3-diphenyldihydrofuran-2(3H)-one 
• 22742-44-5 2-methyl-4,4-diphenyl-tetrahydro-furan 

Relevant articles and documents

Efficient hydrolysis of dithioacetals by the N-fluoro-2,4,6-trimethylpyridinium triflate-water system

Dithioacetals including 1,3-dithianes and 1,3-dithiolanes are efficiently cleaved by the title reagent system to the parent carbonyl compounds. The cleavage of diprotected symmetrical α-diketones and p-phenylenediketones gives monoketones in good yields. Amide, 1,3-dioxolane, disulfide, ester, ether, hydroxy, nitrile, nitro, and sulfide functions are relatively stable under the cleavage conditions but thiols are oxidized to disulfides.

Synthesis and Properties of N-Fluoropyridinium Salts

Various stable N-fluoropyridinium salts with a non- or weakly nucleophilic counter anion such as TfO-, FSO3-, BF4-, ClO4-, CH3SO3- etc., or with an electron-donating or -withdrawing substituent(s) on the pyridine ring were synthesized and their properties investigated.N-Fluoropyridinium-2-sulfonates, N-fluoroquinolinium triflate, and highly hindered N-fluoro-2,6-di-t-butylpyridinium salts were also synthesized.They were synthesized by counter anion displacement reactions of unstable pyridine-F2 conpounds, fluorination of salts of pyridines with protonic acids or silyl esters with F2, and/or fluorination of Lewis acid complexes of pyridines.The scope of each method was examined in detail.Each of the N-fluoropyridinium salts was assigned as the first stable 1:1 salt structure of the pyridine nucleus and halogen atom on the basis of the spectral and elemental analysis.The stability depended on the nucleophilicity or basicity of the counter anions and electronic nature or position of the ring substituents.These results and NMR analyses clearly showed the unstable pyridine-F2 compounds to have N-fluoropyridinium fluoride salt structure.Some N-fluoropyridinium triflates were hydrolyzed and the products were examined, suggesting a unique hydrolysis mechanism.

N-FLUOROPYRIDINIUM TRIFLATE AND ITS ANALOGS, THE FIRST STABLE 1:1 SALTS OF PYRIDINE NUCLEUS AND HALOGEN ATOM

N-Fluoropyridinium salts having non-nucleophilic counter-anions and their derivatives were synthesized by treating pyridine-F2 adducts with strong Broensted acids, their salts or trimethylsilyl esters, of Lewis acids, or by allowing F2 to react with N-trimethylsilylpyridinium salts.