147541-03-5

Basic information

• Product Name: N-FLUORO-4,6-BIS(TRIFLUOROMETHYL)PYRIDINIUM-2-SULFONATE
• Synonyms: N-FLUORO-4,6-BIS(TRIFLUOROMETHYL)PYRIDINIUM-2-SULFONATE;N-FLUORO-4,6-BIS(TRIFLUOROMETHYL)PYRIDINIUM-2-SULPHONATE;1-Fluoro-4,6-bis(trifluoromethyl)pyridin-1-ium-2-sulfonate
• CAS NO: 147541-03-5
• Molecular Formula: C7H2F7NO3S
• Molecular Weight: 313.15
• Mol File: 147541-03-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 173°C (dec.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: N-FLUORO-4,6-BIS(TRIFLUOROMETHYL)PYRIDINIUM-2-SULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: N-FLUORO-4,6-BIS(TRIFLUOROMETHYL)PYRIDINIUM-2-SULFONATE(147541-03-5)
• EPA Substance Registry System: N-FLUORO-4,6-BIS(TRIFLUOROMETHYL)PYRIDINIUM-2-SULFONATE(147541-03-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 147541-03-5(Hazardous Substances Data)

Usage

General Description

N-FLUORO-4,6-BIS(TRIFLUOROMETHYL)PYRIDINIUM-2-SULFONATE is a highly potent and reactive pyridinium salt that is commonly used as a strong fluorinating agent in organic synthesis. It contains a fluorine atom and two trifluoromethyl groups, which make it extremely electron-withdrawing and effective in promoting fluorination reactions. This chemical is often used in the pharmaceutical and agrochemical industries for the synthesis of fluorine-containing organic molecules, which are valuable in the development of new drugs and crop protection agents. Additionally, it has applications in the field of materials science for the modification of surfaces and polymers. Due to its high reactivity and potential hazards, it should be handled with caution and in accordance with proper safety protocols.

InChI:InChI=1/C6H3F4NO3S/c7-6(8,9)4-1-2-5(11(10)3-4)15(12,13)14/h1-3H

Upstream product

• 147541-00-2 4,6-bis(trifluoromethyl)-2-pyridinesulfonic acid 
• 60-29-7 diethyl ether 
• 81565-21-1 6-chloro-2,4-bis(trifluoromethyl)pyridine 

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.