640-57-3

Usage

Uses

p-Methyldiphenyl Sulfone is a derivative of diphenyl sulfone

Synthesis Reference(s)

The Journal of Organic Chemistry, 32, p. 2931, 1967 DOI: 10.1021/jo01284a075Synthesis, p. 283, 1984

InChI:InChI=1/C13H12O2S/c1-11-7-9-13(10-8-11)16(14,15)12-5-3-2-4-6-12/h2-10H,1H3

Upstream product

• 3699-01-2 4-tolyl phenyl sulfide 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 
• 6311-23-5 2-(toluene-4-sulfonylamino)-benzoic acid 
• 103151-64-0 4-[N-(toluene-4-sulfonyl)-anilino]-butyric acid 
• 10506-59-9 dimethyl disulfate 
• 104-15-4 toluene-4-sulfonic acid 
• 71-43-2 benzene 
• 42840-02-8 2-(Toluene-4-sulfonylamino)-benzoyl chloride 
• 60-29-7 diethyl ether 
• 98-09-9 benzenesulfonyl chloride 
• 108-88-3 toluene 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 98-59-9 p-toluenesulfonyl chloride 
• 2674-04-6 diphenyl cadmium 

Downstream Products

• 860699-53-2 2-tosylbenzoic acid 
• 103626-97-7 5-methyl-2,2'-sulfonyl-di-benzoic acid 
• 536-57-2 p-toluene sulfinic acid 
• 5361-54-6 4-(phenylsulfonyl)benzoic acid 
• 7705-63-7 1-(bromomethyl)-4-(phenylsulfonyl)benzene 
• 83859-32-9 4-tolyl phenyl selenide 
• 854637-15-3 2,4-bis-benzenesulfonyl-toluene 
• 101597-95-9 1-benzenesulfonyl-4-diacetoxymethyl-benzene 
• 13333-14-7 4,4'-Di-benzolsulfonyl-stilben 
• 53348-83-7 C₂₈H₂₂O₂S 
• 13350-35-1 p--stilben 
• 13319-05-6 4-Methoxy-4'-benzolsulfonyl-stilben 
• 13333-13-6 p-Phenylsulfonyl-p'-N,N-dimethylamino-stilben 
• 53178-81-7 p-Phenylsulfonyl-α-nitrotoluol 

Relevant academic research and scientific papers

Dispersible porous classical polymer photocatalysts for visible light-mediated production of pharmaceutically relevant compounds in multiple solvents

The dispersibility of photocatalytic polymeric materials is currently a limiting factor for wide scale use. Indeed, the dispersibility of photocatalytic material in solvents dictates its use as heterogenous catalysts, due in part to reagent solubility. Here, we describe a new platform for producing porous polymer photocatalytic nanoparticles that are easily dispersible in a broad range of solvents. Photocatalytic porous classical polymer nanoparticles have been designed, based on classical porous nanoparticles copolymerised with photocatalytic moieties. The combination of both classical and photocatalytic monomers results in an affordable highly photocatalytically effective material, that can be easily dispersed in a wide range of solvents. The versatility and useability of this new material has been demonstrated by photocatalysing a number of pharmaceutically relevant compounds in solvents with varying polarity.

Visible-Light-Mediated Late-Stage Sulfonylation of Boronic Acids via N-S Bond Activation of Sulfonamides

A visible-light-mediated late-stage arylation of N-S bonds in sulfonamides has been developed with using readily available imines as sulfonyl radical source. Diverse complex sulfones could be synthesized by prefunctionalizaiton and subsequent N-S bond ary

Metal-free sulfonylation of arenes with: N -fluorobenzenesulfonimide via cleavage of S-N bonds: expeditious synthesis of diarylsulfones

A novel metal-free sulfonylation of arenes with N-fluorobenzenesulfonimide (NFSI) toward the synthesis of diarylsulfones has been developed. The reaction represents a rare example of sulfonylation reaction using NFSI as an efficient sulfonyl donor and the first example of acid-mediated sulfonylation of unactivated arenes with NFSI via selective cleavage of S-N bonds. This protocol provides a concise approach for the construction of pharmaceutically and biologically important diarylsulfones. Applications in the functionalization of natural products (e.g., β-estradiol) and in the synthesis of a key intermediate to an inhibitor of farnesyl-protein transferase, as well as in the gram-scale synthesis of the EPAC2 antagonist, are demonstrated. This journal is

A Copper(I)-Catalyzed Sulfonylative Hiyama Cross-Coupling

An air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction enabling the formation of diaryl sulfones is described. Starting from aryl silanes, DABSO and aryliodides, the reaction tolerates a large variety of polar functional groups (amines, ketones, esters, aldehydes). Control experiments coupled with DFT calculations shed light on the mechanism, characterized by the formation of a Cu(I)-sulfinate intermediate via fast insertion of a SO2 molecule.

Primary Sulfonamide Functionalization via Sulfonyl Pyrroles: Seeing the N?Ts Bond in a Different Light

Despite common occurrence in molecules of value, methods for transforming sulfonamides are distinctly lacking. Here we introduce easy-to-access sulfonyl pyrroles as synthetic linchpins for sulfonamide functionalization. The versatility of the sulfonyl pyrrole unit is shown by generating a variety of products through chemical, electrochemical and photochemical pathways. Preliminary results on the direct functionalization of primary sulfonamides are also provided, which may lead to new modes of activation.

Sulfonylation of Bismuth Reagents with Sulfinates or SO2through BiIII/BiV Intermediates

Studies to explore the catalytic activities of main-group elements are attractive. We report here our study of sulfonylation of bismuth reagents with sulfinates or SO2 surrogates. Under oxidative conditions, triarylbismuthines and sulfinates were transformed into diaryl sulfones. A transition-metal-like two-electron redox process at the Bi center was achieved in this reaction. Sulfur dioxide generated in situ can also replace sulfinates to deliver the corresponding symmetric diaryl sulfones. A rational mechanism for this reaction was also proposed that involves a Bi(III)-Bi(V) manifold.

Method for synthesizing sulfone compounds under photocatalysis condition

The invention belongs to the technical field of compound preparation, and particularly relates to a method for synthesizing sulfone compounds under a photocatalysis condition. Aromatic hydrazine and sulfinate are used as raw materials, and under the action of alkali and a solvent, a sulfone compound is generated through reaction under the condition of air or oxygen under the illumination of visible light. According to the method disclosed by the invention, aryl hydrazine is used as an arylation reagent, polyacid salt is used as a catalyst or an organic photosensitizer is used as a catalyst, and the sulfones compound can be efficiently synthesized by coupling with sulfinate under the condition of room temperature through visible light irradiation. The method has good substrate universalityand relatively mild reaction conditions, is not only a substitute for synthesizing sulfone compounds by coupling from simple substrates reported at present, but also broadens the new application of the polyacid salt in the field of photocatalysis.

Heterogeneous copper-catalyzed synthesis of diaryl sulfones

A carbon-supported copper nanoparticle (Cu-NP) with high catalytic activity for the synthesis of diaryl sulfones is reported. For the first time, this Cu-NP is proved to be able to effectively promote the reaction of arylboronic acids and arylsulfonyl hydrazides to generate diaryl sulfones at room temperature. The reaction shows excellent substrate universality, and substrates with different substituents can undergo the reaction smoothly, leading to the desired products in good yields. The Cu-NP is found to be made of low valence Cu based on XRD. Hence, the reaction catalyzed by the Cu-NP is believed to involve a Cu-mediated organometallic cycle.

On the important transition of sugar-based surfactant as a microreactor for C-S coupling in water: From micelle to vesicle

A reversible, temperature-induced micelle-to-vesicle transition of a sugar-based pseudogemini surfactant (C11D12) was employed for copper-catalyzed C-S coupling in water. The phase behavior and morphology of the C11D12 aqueous solution were investigated by DLS and cryo-TEM. The aggregates undergo a series of transitions upon increasing the temperature: spherical micelles were initially transformed into large vesicles, but they eventually transformed into smaller vesicles. The vesicular catalytic protocol accommodates an excellent substrate scope with moderate to high yields. The mechanisms of temperature-induced aggregate transition and vesicular catalysis were elucidated by experimental results and DFT calculations. It was revealed that the charge layer of the vesicle grants stronger nucleophilicity to the PhSO2-Cu-D12Ga intermediate. Furthermore, the aqueous reaction medium can be recycled and reused several times after easily separating the precipitated product.

Interfacing sugar-based surfactant micelles and Cu nanoparticles: A nanoreactor for C-S coupling reactions in water

A simple and sustainable synergistic catalytic protocol by interfacing nanomicelles and metal nanoparticles (MNPs) is reported for C-S coupling reactions in water. The sugar-based surfactant GluM was synthesized by introducing a PEG chain to stabilize MNPs and self-assembled to form nanomicelles. Cu2O nanoparticles were generated via in situ reduction of copper salt in an aqueous solution of the sugar-based surfactant. The nature of the interaction between nanomicelles and Cu2O nanoparticles was revealed by XPS, XRD, in situ IR, TEM, and 1H NMR. A broad substrate scope with moderate to excellent yields was documented and the recycling of the GluM/Cu aqueous mixture was surprising.