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804401

Sigma-Aldrich

PyFluor

Synonym(s):

2-Pyridinesulfonyl Fluoride

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About This Item

Empirical Formula (Hill Notation):
C5H4FNO2S
CAS Number:
878376-35-3
Molecular Weight:
161.15
MDL number:
MFCD09265513
UNSPSC Code:
12352101
PubChem Substance ID:
329768867
NACRES:
NA.22

Assay

95% (HPLC)

Quality Level

100

form

solid

mp

29-34 °C

storage temp.

2-8°C

SMILES string

O=S(C1=CC=CC=N1)(F)=O

InChI

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

InChI key

FCFXLXGZHDHJLB-UHFFFAOYSA-N

Application

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.

Legal Information

PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ1036
MKCN2100
MKCG8022
MKCD4989
MKCB9333

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Articles

Deoxyfluorination with 2-Pyridinesulfonyl Fluoride (PyFluor)

The prevalence of organofluorine compounds in industry and drug design necessitates the ability to introduce C–F bonds to molecules.

Related Content

Doyle Group – Professor Product Portal

Research in the Doyle group focuses on two areas: nucleophilic fluorination and nickel catalysis. The Doyle group has developed several reagents that advance these research areas. In fluorination, 2-pyridinesulfonyl fluoride (PyFluor) can be used for the mild deoxyfluorination of primary and secondary alcohols, a procedure which is normally accomplished by the sensitive reagent DAST. In nickel catalysis, the Doyle group has developed a modular, air-stable nickel precatalyst, [(TMEDA)Ni(o-tolyl)Cl], which has broad utility for a wide variety of reactions. This precatalyst can be used in place of Ni(cod)2, NiCl2, as well as other reported precatalysts. Doyle has also reported electron-deficient olefin ligands as a new class of ligand for accelerated reductive elimination. In particular, the sultam-derived ligand Fro-DO has been found to be critical for high yields in the cross-coupling of tertiary aziridines to form quaternary centers.

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