454-66-0

Usage

Uses

Used in Organic Synthesis:
3-Methylbenzenesulfonyl fluoride is used as a reagent for the formation of sulfonamides, which are a class of compounds widely used in pharmacology. Its ability to introduce the sulfonyl fluoride functional group into organic molecules makes it a valuable tool in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
As a precursor for other sulfonyl fluoride derivatives, 3-methylbenzenesulfonyl fluoride contributes to the development of new drugs and pharmaceuticals. Its potential antimicrobial and antifungal properties are currently being studied, which could lead to its use in creating novel treatments for infections.
Used in Research and Development:
3-Methylbenzenesulfonyl fluoride serves as a mild and selective reagent, making it suitable for research purposes where precision and control over chemical reactions are crucial. Its applications in this field can lead to advancements in understanding and creating new chemical entities with therapeutic potential.

Upstream product

• 108-88-3 toluene 
• 108-40-7 toluene-3-thiol 
• 1422-76-0 3-methylbenzenediazonium tetrafluoroborate 
• 17933-03-8 m-tolylboronic acid 
• 58730-68-0 Potassium; toluene-3-sulfonate 
• 15898-38-1 sodium 3-methylbenzenesulfinate 

Relevant academic research and scientific papers

Visible-Light-Mediated Synthesis of Sulfonyl Fluorides from Arylazo Sulfones

Sulfonyl fluorides are useful motifs for a wide range of applications in organic synthesis including sulfur (VI) fluoride exchange-based “click chemistry.” Herein, a visible-light-mediated synthesis of sulfonyl fluorides from arylazo sulfones is described. In the present study, K2S2O5 and N-fluorobenzenesulfonimide (NFSI) were used as the sulfonyl source and fluorinating agent, respectively, for visible-light-mediated fluorosulfonylation of arylazo sulfones to prepare various sulfonyl fluorides in 60–85% yield. This protocol is a synthetic approach to provide useful sulfonyl fluoride structures at room temperature. (Figure presented.).

Redox-Neutral Organometallic Elementary Steps at Bismuth: Catalytic Synthesis of Aryl Sulfonyl Fluorides

A Bi-catalyzed synthesis of sulfonyl fluorides from the corresponding (hetero)aryl boronic acids is presented. We demonstrate that the organobismuth(III) catalysts bearing a bis-aryl sulfone ligand backbone revolve through different canonical organometallic steps within the catalytic cycle without modifying the oxidation state. All steps have been validated, including the catalytic insertion of SO2 into Bi-C bonds, leading to a structurally unique O-bound bismuth sulfinate complex. The catalytic protocol affords excellent yields for a wide range of aryl and heteroaryl boronic acids, displaying a wide functional group tolerance.

Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride

Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based "click chemistry" is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl fluorides using thiols or disulfides, as widely available starting materials, in combination with KF, as an inexpensive, abundant and safe fluoride source. No additional oxidants nor additional catalysts are required and, due to mild reaction conditions, the reaction displays a broad substrate scope, including a variety of alkyl, benzyl, aryl and heteroaryl thiols or disulfides.

One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides

A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium-catalyzed sulfonylation of aryl bromides using DABSO as an SO2 source, followed by in situ treatment of the resultant sulfinate with the electrophilic fluorine source NFSI. This sequence represents the first general method for the sulfonylation of aryl bromides, and offers a practical, one-pot alternative to previously described syntheses of sulfonyl fluorides, allowing rapid access to these biologically important molecules. Excellent functional group tolerance is demonstrated, with the transformation successfully achieved on a number of active pharmaceutical ingredients, and their precursors. The preparation of peptide-derived sulfonyl fluorides is also demonstrated.

Orthoamides, LXIV [1]. Formylation of aromatic compounds by tris(dichloromethyl)amine and oligoformylamine derivatives in the presence of superacids

Tris(dichloromethyl)amine (4), triformamide (1) and tris(diformylamino) methane ( formyl-aalen ) (2) can be activated by addition of trifluoromethanesulfonic acid. The formylating systems thus formed transform activated aromatic compounds, such as toluene, anisole or 2,4-dimethoxybenzene to the corresponding aldehydes. The formylating ability of systems from 4 and superacids, such as FSO3H, FSO3H/SbF5, C 4F9SO3H, and mixtures of aluminum chloride with C4F9SO3H and chlorosulfonic acid, respectively, is compared. In general, low reaction temperatures (-20 to -10°C) are necessary to obtain aldehydes with acceptable to good yields. Remarkably, at higher temperatures (～ 100°C) compound 4 can also act as a formylating agent in the presence of suitable zeolites, as e. g. zeolite HBEA. Reaction mechanisms of the new formylation reactions are proposed.

NOVEL COMPOUNDS

The present invention relates to novel indole derivatives such as compounds of the formula (I): which possess antagonist potency at the 5-HT6 receptor and the use of such compounds or pharmaceutically acceptable salts or solvates thereof in the treatment of Alzheimer's disease and other CNS disorders.

OXIDATION OF METHYL-SUBSTITUTED BENZENESULFONYL FLUORIDES IN THE PbO2-HSO3F SYSTEM

The transformations of the sulfonyl fluorides of methyl-substituted benzenes in the PbO2-HSO3F system were studied.They take place through a stage involving the one-electron oxidation of the substrate to aromatic radical-cations.One of the transformation paths of the latter is realized through the elimination of a proton from the methyl groups involved to the greatest degree in the delocalization of the unpaired electron.This leads to the formation of diarylmethanes and the fluorosulfonates of substituted benzyl alcohols, which give substituted tolylsultones and benzyl alcohols during hydrolysis of the acid solution and methyl ethers of benzyl alcohols during methanolysis.The other path, which arises during localization of the unpaired electron in the unsubstituted positions of the benzene ring, leads to biaryls.

KINETIC INVESTIGATION OF THE S-FLUORINATION OF ARENESULFINATES WITH PERCHLORYL FLUORIDE

The effect of substituents and solvents on the kinetics of S-fluorination of sodium arenesulfinates with perchloryl fluoride was investigated.Alternative fluorination mechanisms were examined, and it was found that the mechanism is SN2 substitution at the fluorine atom.