130433-68-0

Usage

Uses

Used in Organic Chemistry:
1-Fluoro-2,6-dichloropyridinium triflate is used as a fluorinating agent for the transformation of thioglycosides into o-glycoside, glycosyl azide, and sulfoxide. It is also employed in electrolytic partial fluorination and diastereoselective anodic fluorination processes.
Used in Electrochemical Fluorination:
1-Fluoro-2,6-dichloropyridinium triflate is used as a reagent for regioselective electrochemical fluorination, which allows for the selective introduction of fluorine atoms into specific positions in organic molecules.
Used in Fluorination of Alkenes:
1-Fluoro-2,6-dichloropyridinium triflate is used in the fluorination of alkenes with N-F type reagents, enabling the synthesis of various fluorinated organic compounds with potential applications in pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C5H3Cl2FN.CHF3O3S/c6-4-2-1-3-5(7)9(4)8;2-1(3,4)8(5,6)7/h1-3H;(H,5,6,7)/q+1;/p-1

Upstream product

• 2402-78-0 2,6-dichloropyridine 
• 1493-13-6 trifluorormethanesulfonic acid 

Downstream Products

• 17228-74-9 2,6-dichloro-4-hydroxypyridine 
• 135183-03-8 N-Fluoro-6-chloro-2-pyridone 

Relevant academic research and scientific papers

Preparation of fluorohalophenols and N-acyfluorohaloanilines

Chloro and bromophenols and N-acylanilines are fluorinated in an ortho or para position with an N-fluoropyridinium salt to obtain fluorohalophenols and N-acylfluorohaloanilines, which can be further converted to fluorophenols and N-acylfluoroanilines by reduction. Thus, o-fluorophenol is obtained by fluorination of p-bromophenol with 2-chloro-6-(trichloromethyl)-pyridinium fluoroborate and reduction of the product obtained with sodium formate and a palladium catalyst. N-fluoropyridinium salts having trichloromethyl substituents are disclosed.

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.