147540-88-3

Basic information

• Product Name: N-FLUORO-4-METHYLPYRIDINIUM-2-SULFONATE
• Synonyms: DAIKIN MEC-02;N-FLUORO-4-METHYLPYRIDINIUM-2-SULFONATE;N-FLUORO-4-METHYLPYRIDINIUM-2-SULPHONATE;Pyridinium,1-fluoro-4-methyl-2-sulfo-, inner salt
• CAS NO: 147540-88-3
• Molecular Formula: C₆H₆FNO₃S
• Molecular Weight: 191.18
• Mol File: 147540-88-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 203-208°C (dec.)
• Appearance: /
• CAS DataBase Reference: N-FLUORO-4-METHYLPYRIDINIUM-2-SULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: N-FLUORO-4-METHYLPYRIDINIUM-2-SULFONATE(147540-88-3)
• EPA Substance Registry System: N-FLUORO-4-METHYLPYRIDINIUM-2-SULFONATE(147540-88-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 147540-88-3(Hazardous Substances Data)

Usage

General Description

N-FLUORO-4-METHYLPYRIDINIUM-2-SULFONATE is a chemical compound which is commonly used as a fluorinating agent in various organic synthesis reactions. It is a quaternary ammonium salt with a fluorine atom attached to the nitrogen atom and a sulfonate group attached to the pyridinium ring. N-FLUORO-4-METHYLPYRIDINIUM-2-SULFONATE is highly reactive and is often used to introduce fluorine atoms into organic molecules, as fluorine is a highly electronegative element and its introduction can significantly alter the properties of the target molecule. N-FLUORO-4-METHYLPYRIDINIUM-2-SULFONATE is also used as a mild and selective fluorinating reagent in various pharmaceutical and agrochemical applications.

InChI:InChI=1/C6H6FNO3S/c1-5-2-3-8(7)6(4-5)12(9,10)11/h2-4H,1H3

Upstream product

• 18616-04-1 4-methylpyridine-2-sulfonic acid 

Downstream Products

• 234759-81-0 2-(Cyclopropylthio)-1-(2,4-difluorophenyl)-2,2-difluoro-1-ethanone 
• 192862-11-6 1-(2,4-difluorophenyl)-2,2-difluoro-2-(methylthio)-1-ethanone 
• 201034-36-8 2,2-difluoro-2',4'-difluoro-2-(2-methoxyethyl)thioacetophenone 

Relevant articles and documents

Highly Selective Fluorinating Agents: A Counteranion-Bound N-Fluoropyridinium Salt System

A series of alkyl- or (trifluoromethyl)-substituted N-fluoropyridinium-2-sulfonates 2a-h, differing in fluotinating power, were synthesized, and assessment was made of the effectiveness of each selective fluorinating agent.N-Fluoropyridinium-3- and -4-sulfonates 3 and 4 were also synthesized.Power-variables 2a-h were found to be highly selective fluorinating agents for a wide range of nucleophilic substrates such as activated aromatics, enol trialkylsilyl and alkyl ethers, active methylene compounds, activated olefins, and sulfides.Thus, phenol, naphthol, phenylurethane, and the trimethylsilyl ether of phenol were exclusively or highly selectively fluorinated at the o-position with 2f-h.Conjugated enol trialkylsilyl ethers of a steroid were regioselectively fluorinated at the 6-position with moderately powerful 2b-e.This regioselectivity increased with the bulkiness of the silyl part, and with the most bulky triisopropylsilyl group exclusive 6-fluorination was achieved.Preferential β-stereoselective fluorination at the 6-position was observed.N-Fluoropyridinium-2-sulfonates were activated with an acid.This acid-catalyzed fluorination led to the preferential p-fluorination of anisole.The present results can be explained based on the capacity of the 2-sulfonate anion to interact with the hydroxy group of phenol or naphthol, NH group of phenylurethane, silicon atoms of silyl ethers, or protons of acids.