107263-95-6

Basic information

• Product Name: 1-FLUOROPYRIDINIUM TRIFLATE
• Synonyms: N-FLUOROPYRIDINIUM TRIFLATE;N-FLUOROPYRIDINIUM TRIFLUOROMETHANESULFONATE;N-FLUOROPYRIDINIUM TRIFLUOROMETHANESULPHONATE;1-FLUOROPYRIDINIUM TRIFLATE;1-FLUOROPYRIDINIUM TRIFLUOROMETHANESULFONATE;PYRIDINIUM,1-FLUORO-TRIFLUOROMETHANESULFONIC ACID(1:1);Pyridinium, 1-fluoro-, salt with trifluoromethanesulfonic acid (1:1);N-Fluoropyridinium trifluoromethanesulphonate 99%
• CAS NO: 107263-95-6
• Molecular Formula: CF₃O₃S*C₅H₅FN
• Molecular Weight: 247.17
• Product Categories: Electrophilic Fluorinating Reagents;Fluorinating Reagents;Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds;Fluorination;Halogenation;Pyridinium Compounds;Synthetic Organic Chemistry;Chemical Synthesis;Fluorination Reagents;Synthetic Reagents
• Mol File: 107263-95-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 185-186 °C(lit.)
• Boiling Point: 162 °C at 760 mmHg
• Appearance: White to off-white/Crystalline Powder or Needles
• Density: 1.5493 (estimate)
• Vapor Pressure: 1.14mmHg at 25°C
• Storage Temp.: 0-6°C
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 4222821
• CAS DataBase Reference: 1-FLUOROPYRIDINIUM TRIFLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-FLUOROPYRIDINIUM TRIFLATE(107263-95-6)
• EPA Substance Registry System: 1-FLUOROPYRIDINIUM TRIFLATE(107263-95-6)

Safety Data

• Hazard Codes: C,Xi
• Statements: 35-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 107263-95-6(Hazardous Substances Data)

Usage

Description

1-Fluoropyridinium triflate, also known as N-fluoropyridinium trifluoromethanesulfonate, is a white to off-white crystalline powder or needles that serves as a general-purpose electrophilic fluorinating reagent. It is a versatile compound with tunable fluorinating properties, where the electronic nature of the substituents on the ring dictates the potency and selectivity of the reagent.

Uses

1. Used in Organic Chemistry:
1-Fluoropyridinium triflate is used as an electrophilic fluorinating reagent for efficient fluorination of various aromatics, carbanions, vinyl esters, alkyls, and enamines. Its tunable fluorinating system allows for precise control over the reaction, making it a valuable tool in organic synthesis.
2. Used in Medicinal Chemistry:
1-Fluoropyridinium triflate is employed as a reactant for Pd-catalyzed arylation reactions, which are crucial in the synthesis of complex organic molecules, including pharmaceutical compounds. Its ability to introduce fluorine atoms into molecules can significantly impact the biological activity and pharmacokinetic properties of these compounds.
3. Used in Research and Development:
In addition to its practical applications, 1-Fluoropyridinium triflate is also used as a subject of study for a review of electrophilic N-F fluorinating agents. This research helps to further understand the reactivity and potential applications of this class of compounds in various fields, including materials science, pharmaceuticals, and agrochemicals.

InChI:InChI=1/C5H5FN.CHF3O3S/c6-7-4-2-1-3-5-7;2-1(3,4)8(5,6)7/h1-5H;(H,5,6,7)/q+1;/p-1

Upstream product

• 110-86-1 pyridine 
• 1493-13-6 trifluorormethanesulfonic acid 
• 2926-30-9 sodium triflate 
• 33454-82-9 lithium trifluoromethanesulfonate 
• 88188-06-1 trimethyl((trifluoromethyl)sulfonyl)silane 
• 84355-13-5 N-Trimethylsilylpyridinium trifluoromethanesulfonate 
• 2926-29-6 Langlois reagent 

Downstream Products

• 65007-00-3 pyridin-2-yl trifluoromethanesulfonate 
• 372-48-5 2-fluoropyridine 
• 111399-90-7 2-<(4-fluorobutyl)oxy>pyridine 
• 111399-91-8 2-[4-(4-Fluoro-butoxy)-butoxy]-pyridine 
• 150059-62-4 tert-butyl 2-(pyridin-2-yl)acetate 
• 111399-92-9 2-[2-(2-Fluoro-ethoxy)-ethoxy]-pyridine 
• 55484-05-4 2-(furan-3’-yl)pyridine 
• 55484-03-2 2-(2'-furyl)pyridine 
• 108161-26-8 6-fluoro-1-methoxy-1-cyclohexene 
• 60839-94-3 2-fluoro-methylthiobenzene 
• 21179-04-4 pyridinium triflate 
• 65325-65-7 1-chloro-4-[(fluoromethyl)sulfanyl]benzene 
• 1628-89-3 2-methoxypyridine 
• 73322-01-7 2-((4-nitrophenyl)thio)pyridine 

Relevant articles and documents

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.

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: An electrophilic fluorinating agent

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