878376-35-3

Basic information

• Product Name: PYRIDINE-2-SULFONYL FLUORIDE
• Synonyms: PYRIDINE-2-SULFONYL FLUORIDE;2-Pyridinesulfonyl fluoride;PyFluor
• CAS NO: 878376-35-3
• Molecular Formula: C5H4FNO2S
• Molecular Weight: 161.15
• Mol File: 878376-35-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 29-34°C
• Boiling Point: 234.939°C at 760 mmHg
• Flash Point: 95.888°C
• Appearance: /
• Density: 1.421g/cm³
• Vapor Pressure: 0.079mmHg at 25°C
• Refractive Index: 1.502
• Storage Temp.: 2-8°C
• PKA: -3.93±0.19(Predicted)
• CAS DataBase Reference: PYRIDINE-2-SULFONYL FLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PYRIDINE-2-SULFONYL FLUORIDE(878376-35-3)
• EPA Substance Registry System: PYRIDINE-2-SULFONYL FLUORIDE(878376-35-3)

Safety Data

• Hazard Codes: C
• RIDADR: UN 3261 8 / PGII
• TSCA: No
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 878376-35-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 878376-35-3 differently. You can refer to the following data:
1. Novel thermally stable deoxyfluorination reagent with a broad substrate scope of alcohols.
2. 2-pyridinesulfonyl fluoride can be used for the deoxyfluorination of primary and secondary alcohols in combination with an amidine or guanidine base. In comparison with other common deoxyfluorination reagents, for example, DAST exhibits less elimination side products in direct comparison on certain substrates.

InChI:InChI=1/C5H4FNO2S/c6-10(8,9)5-3-1-2-4-7-5/h1-4H

Upstream product

• 2637-34-5 2-Sulfanylpyridine 
• 66715-65-9 pyridine-2-sulfonyl chloride 

Downstream Products

• 5957-90-4 4-(2-pyridinyl)anisole 

Relevant articles and documents

A Unified Strategy for Arylsulfur(VI) Fluorides from Aryl Halides: Access to Ar-SOF3 Compounds

A convenient protocol to selectively access various arylsulfur(VI) fluorides from commercially available aryl halides in a divergent fashion is presented. Firstly, a novel sulfenylation reaction with the electrophilic N-(chlorothio)phthalimide (Cl-S-Phth) and arylzinc reagents afforded the corresponding Ar-S-Phth compounds. Subsequently, the S(II) atom was selectively oxidized to distinct fluorinated sulfur(VI) compounds under mild conditions. Slight modifications on the oxidation protocol permit the chemoselective installation of 1, 3, or 4 fluorine atoms at the S(VI) center, affording the corresponding Ar-SO2F, Ar-SOF3, and Ar-SF4Cl. Of notice, this strategy enables the effective introduction of the rare and underexplored -SOF3 moiety into various (hetero)aryl groups. Reactivity studies demonstrate that such elusive Ar-SOF3 can be utilized as a linchpin for the synthesis of highly coveted aryl sulfonimidoyl fluorides (Ar-SO(NR)F).

PyFluor: A low-cost, stable, and selective deoxyfluorination reagent

We report an inexpensive, thermally stable deoxyfluorination reagent that fluorinates a broad range of alcohols without substantial formation of elimination side products. This combination of selectivity, safety, and economic viability enables deoxyfluorination on preparatory scale. We employ the [18F]-labeled reagent in the first example of a no-carrier-added deoxy-radiofluorination.