444-31-5

Basic information

• Product Name: o-Toluenesulfonyl fluoride
• CAS NO: 444-31-5
• Molecular Formula: C₇H₇FO₂S
• Molecular Weight: 174.196
• Mol File: 444-31-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 227.4°Cat760mmHg
• Flash Point: 91.3°C
• Density: 1.276g/cm³
• CAS DataBase Reference: o-Toluenesulfonyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: o-Toluenesulfonyl fluoride(444-31-5)
• EPA Substance Registry System: o-Toluenesulfonyl fluoride(444-31-5)

Safety Data

• Hazardous Substances Data: 444-31-5(Hazardous Substances Data)

Upstream product

• 137-06-4 2-thiocresol 
• 133-59-5 Toluene-2-sulfonyl chloride 
• 368-43-4 phenylsulfonyl fluoride 
• 74-88-4 methyl iodide 
• 108-88-3 toluene 
• 7789-21-1 fluorosulphonic acid 
• 15898-37-0 sodium 2-methylbenzenesulfinate 
• 88-19-7 methyl 2-(aminosulfonyl)benzoate 
• 143893-31-6 potassium toluenesulfonate 

Downstream Products

• 91340-63-5 N-(2-methylphenylsulfonyl)-N-(tert-butyl)amine 
• 643-58-3 2-methylbiphenyl 
• 96892-87-4 3-(2-Fluorosulfonyl-benzyl)-2-methyl-benzenesulfonyl fluoride 
• 4430-23-3 3H-benzo[c][1,2]oxathiole-1,1-dioxide 

Relevant articles and documents

Synthesis of Sulfonyl Fluorides from Sulfonamides

A simple and practical synthesis of sulfonyl fluorides from sulfonamides is reported. The method capitalizes on the formation of the sulfonyl chloride by virtue of the reaction of Pyry-BF4 and MgCl2, and subsequent in situ conversion to the more robust and stable sulfonyl fluoride by the presence of KF. The mild conditions and high chemoselectivity of the protocol enable the late-stage formation of sulfonyl fluorides from densely functionalized molecules.

SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase

Sulfur fluoride exchange (SuFEx) has emerged as the new generation of click chemistry. We report here a SuFEx-enabled, agnostic approach for the discovery and optimization of covalent inhibitors of human neutrophil elastase (hNE). Evaluation of our ever-growing collection of SuFExable compounds toward various biological assays unexpectedly revealed a selective and covalent hNE inhibitor: benzene-1,2-disulfonyl fluoride. Synthetic derivatization of the initial hit led to a more potent agent, 2-(fluorosulfonyl)phenyl fluorosulfate with IC50 0.24 μM and greater than 833-fold selectivity over the homologous neutrophil serine protease, cathepsin G. The optimized, yet simple benzenoid probe only modified active hNE and not its denatured form.

Sulfur(VI) fluoride compounds and methods for the preparation thereof

This application describes a compound represented by Formula (I): (I) wherein: Y is a biologically active organic core group comprising one or more of an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group, to which Z is covalently bonded; n is 1, 2, 3, 4 or 5; m is 1 or 2; Z is O, NR, or N; X1 is a covalent bond or —CH2CH2—, X2 is O or NR; and R comprises H or a substituted or unsubstituted group selected from an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group. Methods of preparing the compounds, methods of using the compounds, and pharmaceutical compositions comprising the compounds are described as well.