5033-22-7

Usage

Uses

Used in Microelectronics Industry:
(Pyrrolidinyl)(phenyl)sulfone is used as a photo-activated compound for the development of photoresists. Its photo-activated properties make it a promising candidate in the creation of high-resolution photoresists, which are crucial for the patterning process in microelectronics manufacturing.
Used in Organic Synthesis:
In the realm of organic synthesis, (Pyrrolidinyl)(phenyl)sulfone serves as a valuable intermediate. It is particularly useful in the preparation of various heterocyclic compounds, contributing to the synthesis of complex organic molecules with potential applications in pharmaceuticals and other chemical industries.
Used in Pharmaceutical Research:
(Pyrrolidinyl)(phenyl)sulfone is being investigated for its potential anti-inflammatory and anti-cancer properties. Its ability to modulate biological pathways and exhibit therapeutic effects positions it as a candidate for further research and development in the pharmaceutical industry, with the aim of discovering new treatments for inflammatory conditions and cancer.
Used in Material Science:
(Pyrrolidinyl)(phenyl)sulfone's unique structural features and chemical properties also make it a subject of interest in material science. Researchers are exploring its potential applications in the development of new materials with specific properties, such as improved stability or reactivity, which could be beneficial in various industrial applications.

InChI:InChI=1/C10H13NO2S/c12-14(13,11-8-4-5-9-11)10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2

Upstream product

• 123-75-1 pyrrolidine 
• 98-09-9 benzenesulfonyl chloride 
• 16851-82-4 N-phenylsulfonylpyrrole 
• 75-09-2 dichloromethane 
• 121434-38-6 phenyliodonium bis(phenylsulfonyl)-methylide 
• 182356-71-4 1-benzenesulfinyl-pyrrolidine 
• 929000-58-8 1-((2-bromophenyl)sulfonyl)pyrrolidine 
• 5535-48-8 PVS 
• 7335-06-0 1-ethylpyrrolidine 
• 873-55-2 sodium benzenesulfonate 
• 80-17-1 benzenesufonyl hydrazide 
• 108-98-5 thiophenol 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 1212-08-4 S-Phenyl benzenethiosulfonate 

Downstream Products

• 88000-68-4 1-benzenesulfonyl-pyrrolidin-2-one 
• 1312718-23-2 ethyl 2-(3-iodo-2,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)phenylthio)-1H-pyrrol-1-yl)acetate 
• 1312718-22-1 1,2-bis(2-(pyrrolidin-1-ylsulfonyl)phenyl)disulfane 
• 1219449-56-5 sodium hydroxy(2-(pyrrolidin-1-ylsulfonyl)phenyl)methanesulfonate 

Relevant academic research and scientific papers

Development of succinimide-based inhibitors for the mitochondrial rhomboid protease PARL

While the biochemistry of rhomboid proteases has been extensively studied since their discovery two decades ago, efforts to define the physiological roles of these enzymes are ongoing and would benefit from chemical probes that can be used to manipulate the functions of these proteins in their native settings. Here, we describe the use of activity-based protein profiling (ABPP) technology to conduct a targeted screen for small-molecule inhibitors of the mitochondrial rhomboid protease PARL, which plays a critical role in regulating mitophagy and cell death. We synthesized a series of succinimide-containing sulfonyl esters and sulfonamides and discovered that these compounds serve as inhibitors of PARL with the most potent sulfonamides having submicromolar affinity for the enzyme. A counterscreen against the bacterial rhomboid protease GlpG demonstrates that several of these compounds display selectivity for PARL over GlpG by as much as two orders of magnitude. Both the sulfonyl ester and sulfonamide scaffolds exhibit reversible binding and are able to engage PARL in mammalian cells. Collectively, our findings provide encouraging precedent for the development of PARL-selective inhibitors and establish N-[(arylsulfonyl)oxy]succinimides and N-arylsulfonylsuccinimides as new molecular scaffolds for inhibiting members of the rhomboid protease family.

AEROBIC OXIDATIVE SYNTHESIS OF SULFONAMIDE USING Cu CATALYST

The present invention relates to a method for oxidative synthesis of sulfonamides using copper catalysts. , Oxygen (O) is used. 2 The oxidative synthesis of sulfonamides (1) comprises reacting a 2 th or sulfonyl hydrazide primary amine with a sulfonyl hydrazide (sulfonamide) with a copper catalyst on a solvent under the conditions in which the sulphonamide is fed. The oxidation coupling of the present invention showed extensive substrate ranges in an amine comprising a 2 primary amine, 1 primary amine and amine hydrochloride salt. It is worth notable that non-reactive aliphatic sulfonyl hydrazides in previously reported anaerobic systems can be used for the aerobic oxidation coupling of the present invention. The oxidation coupling of the present invention has been more effective on large scale.

Method for preparing N-sulfonyl tetrahydropyrrole compound by using gold complex

The invention relates to a method for preparing an N-sulfonyl tetrahydropyrrole compound by using a gold complex, which comprises the following step of: reacting a sulfonamide compound and a tetrahydrofuran compound as raw materials with a gold complex containing an ortho-carborane Schiff base ligand as a catalyst at room temperature to obtain the N-sulfonyl tetrahydropyrrole compound. Compared with the prior art, the method has the advantages that the gold complex containing the ortho-carborane Schiff base ligand is adopted as the catalyst, the sulfonamide compound and the tetrahydrofuran compound can be catalyzed to react under the room temperature condition to prepare the N-sulfonyl tetrahydropyrrole compound, the usage amount of the catalyst is low, the reaction condition is mild, the reaction rate is high, the product yield is high, the substrate is high in universality, the raw materials are cheap and easy to obtain, and the method has a wide application prospect in industry.

Cyanide-Mediated Synthesis of Sulfones and Sulfonamides from Vinyl Sulfones

We report a facile synthesis of sulfones, β-keto sulfones, and sulfonamides from vinyl sulfones via an addition-elimination sequence where in situ generation of nucleophilic sulfinate ion is mediated by cyanide. The use vinyl sulfones renders high selectivity for S -alkylation to produce sulfones in high yields. In the presence of N -bromosuccinimide, primary and secondary amines underwent sulfonamide formation. A preliminary mechanistic study showed the formation of acrylonitrile as an innocent byproduct, without interfering with the desired reaction pathway while generating a sulfinate nucleophile.

Synthesis method of beta-aryl sulfonyl enamine compound

The invention belongs to the technical field of organic synthesis. The invention relates to the technical field of organic synthesis, in particular to a synthesis method of a beta-aryl sulfonyl enamine compound, which comprises the following steps: in an air environment, with a sodium benzenesulfinate derivative and tertiary amine as substrates, carrying out anodic oxidation coupling reaction in amixture of an electrolyte and a solvent to obtain the beta-aryl sulfonyl enamine compound. The synthesis method of the beta-aryl sulfonyl enamine compound provided by the invention is free of metal,oxidant and halogen, the whole synthesis process is harmless to the environment, and a variety of beta-aryl sulfonyl enamine compounds with satisfactory yield can be obtained.

Efficient and Practical Synthesis of Sulfonamides Utilizing SO2 Gas Generated on Demand

A simple and practical protocol was developed for the synthesis of sulfonamides by reacting organometallic reagents with SO2 gas generated on demand. SO2 was generated from readily available reagents safely in a highly contained and controlled fashion. The protocol allows the synthesis of sulfonamides without using either atom-inefficient SO2 surrogates or a SO2 cylinder that requires stringent storage regulations in the laboratory. The protocol was successfully applied to the synthesis of sildenafil.

Iodine-catalyzed sulfonylation of sulfonyl hydrazides with: Tert -amines: A green and efficient protocol for the synthesis of sulfonamides

This study provides a direct, sustainable and eco-friendly method for the synthesis of various sulfonamides via the sulfonylation of sulfonyl hydrazides with tert-amines. The method utilizes sulfonyl hydrazides to oxidize and couple with tertiary amines through selective cleavage of C-N bonds. In this reaction, molecular iodine was used as the catalyst and t-butyl hydroperoxide was used as the oxidant.

Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols

Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.

Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols

Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.

Hypervalent Iodine Mediated Sulfonamide Synthesis

A new metal-free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group-transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram-scale. The reaction mechanism was investigated by ESI-MS and DFT calculations.