65007-00-3

Usage

Uses

Used in Chemical Synthesis:
2-PYRIDYL TRIFLUOROMETHANESULFONATE is used as a reagent for the preparation of pyridinium salts, specifically [R-iso-BIPY-H]+[OTF]salts. These salts are formed through the reaction involving 2-Pyridyl triflate and N-(2-pyridyl)-R-pyridine-2-ylidene compounds, where R can be 4-H, 4-tert-butyl, 4-dimethylamino, or 5-dimethylamino. The trifluoromethanesulfonate ion (OTf-) plays a crucial role in the formation of these salts, which have potential applications in various fields such as materials science and pharmaceuticals.

InChI:InChI=1/C6H4F3NO3S/c7-6(8,9)14(11,12)13-5-3-1-2-4-10-5/h1-4H

Upstream product

• 109-99-9 tetrahydrofuran 
• 107263-95-6 N-fluoropyridinium triflate 
• 123-91-1 1,4-dioxane 
• 110-00-9 furan 
• 75-05-8 acetonitrile 
• 67-56-1 methanol 
• 78715-82-9 1,2,3,5-Thiatriazolo<5.4a>pyridin-3-oxide 
• 2926-30-9 sodium triflate 
• 504-29-0 2-aminopyridine 
• 1493-13-6 trifluorormethanesulfonic acid 
• 108-88-3 toluene 
• 71-43-2 benzene 
• 64-17-5 ethanol 
• 109-89-7 diethylamine 

Downstream Products

• 133559-47-4 1-(2-Pyridyl)-4-(4-methoxyphenyl)butane-1,4-dione 
• 86521-05-3 2-(trimethylsilylethynyl)pyridine 
• 3319-99-1 2'-(2-thienyl)pyridine 
• 581-50-0 2,3'-bipyridine 
• 54015-96-2 6-methoxy-2-(2-pyridinyl)pyridine 
• 19848-68-1 2-[2-(diphenylmethylene)hydrazinyl]pyridine 
• 1008-89-5 2-phenylpyridine 
• 109-04-6 2-bromo-pyridine 
• 4282-47-7 2-(4-nitrophenyl)pyridine 
• 173681-56-6 1-(4-(pyridin-2-yl)phenyl)ethanone 
• 98061-21-3 4-pyridin-2-yl-benzoic acid methyl ester 
• 32111-34-5 4-(pyridine-2-yl)benzonitrile 
• 93324-66-4 2-(4-phenylphenyl)pyridine 
• 4467-06-5 2-(4-methylphenyl)pyridine 

Relevant academic research and scientific papers

A Novel Convenient Synthesis of Pyridinyl and Quinolinyl Triflates and Tosylates via One-Pot Diazotization of Aminopyridines and Aminoquinolines in Solution

The first effective and simple method for the direct one-pot transformation of 2-, 3-, and 4-aminopyridines, 2,6-diaminopyridines, and 2-aminoquinoline into the corresponding pyridinyl and quinolinyl trifluoromethanesulfonates and tosylates in solvents was developed. The procedure involves diazotization of the heterocyclic amines with sodium nitrite in mixed hexane-DMSO or hexane-DMF solutions in the presence of trifluoromethanesulfonic acid or p-toluenesulfonic acid.

Novel base-initiated reactions of N-substituted pyridinium salts

Reaction of N-fluoropyridinium triflate with a base in dichloromethane gave 2-chloropyridine as the major product along with 2-pyridyl triflate and 2-fluoropyridine, regardless of the nature of the base. This base-initiated reaction was also shown to take place similarly in other halogenated alkanes, ethers, a nitrile, aromatics, a ketone, vinyl ethers, alcohols and trimethylsilyl acetate as solvents to give pyridine derivatives substituted with a solvent molecule (s) at the 2-position. N-(Trifluoromethanesulfonyloxy)-and (benzenesulfonyloxy) pyridinium salts were found to undergo the same base-initiated reaction. These reactions may be explained by a postulated singlet carbene (canonical formula 11b) produced through proton abstraction of N-substituted pyridinium salts. A similar carbene reaction may thus likely occur in the thermal decomposition of thiatriazole 10. Ab initio MO calculations revealed the structure and properties of the labile deprotonated N-fluoropyridinium cation and supported the carbene intermediate reaction mechanism rather than a pyridynium or pyridyl cation mechanism. Quarroz's reports on the reactions of picolinic acid N-oxide and the reported reactions of pyridines with F2, CH3COOF or CsSO4F in solvents may be explained by this carbene mechanism.

Preparation of 2-Fluoropyridines via Base-Induced Decomposition of N-Fluoropyridinium Salts

N-Fluoropyridinium salts with either BF4-, SbF6-, or PF6- as a counteranion were treated with excess base such as triethylamine at room temperature to give 2-fluoropyridine in good yield.This method was succesfully applied to the preparation of 2-fluoropyridine derivatives possessing electron-donating or -withdrawing substituents using substituted N-fluoropyridinium tetrafluoroborates.Pyridine-F2 compounds produced through reactions of pyridines with molecular fluorine were also treated with base to give 2-fluoropyridines but in low yields.These reactions are considered to occur through a carbene mechanism as follows: a novel N-F-containing cyclic carbene (3), generated from the N-fluoropyridinium salts by 2-proton abstraction, reacts with fluorine atoms from counteranions such as BF4-, SbF6-, or PF6-, followed by elimination of F- from the N-F moiety, to yield 2-fluoropyridines.Previously reported findings in reactions of pyridines with molecular fluorine are explained on the basis of this mechanism.

BASE-INITIATED REACTIONS OF N-FLUOROPYRIDINIUM SALTS; A NOVEL CYCLIC CARBENE PROPOSED AS A REACTIVE SPECIES

A new type of base-initiated reactions of pyridinium salts was found and a novel cyclic carbene was proposed as the reactive species.