599-66-6

Usage

Uses

Used in Organic Synthesis:
DI-P-TOLYL SULFONE is used as a key intermediate in the synthesis of various organic compounds, including isomeric p-tolylpyridines (α, β, and γ). It is synthesized through photochemical decomposition, which allows for the production of these valuable compounds.
Used in OLED Material Preparation:
In the electronics industry, DI-P-TOLYL SULFONE is used in the preparation method of OLED (Organic Light Emitting Diode) materials. It plays a crucial role in improving the luminous efficiency of these materials, leading to better performance and longer lifespan of OLED devices.

Purification Methods

Crystallise the sulfone repeatedly from Et2O or EtOH. It has been purified by zone melting. [Beilstein 6 H 419, 6 II 395, 6 III 1405, 6 IV 2174.]

InChI:InChI=1/C14H14O2S/c1-11-3-7-13(8-4-11)17(15,16)14-9-5-12(2)6-10-14/h3-10H,1-2H3

Upstream product

• 1774-35-2 di(p-tolyl) sulfoxide 
• 6311-23-5 2-(toluene-4-sulfonylamino)-benzoic acid 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 104-15-4 toluene-4-sulfonic acid 
• 108-88-3 toluene 
• 98-59-9 p-toluenesulfonyl chloride 
• 80-48-8 methyl p-toluene sulfonate 
• 10506-59-9 dimethyl disulfate 
• 1445-73-4 1-Methyl-4-piperidone 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 620-94-0 di-(p-tolyl)sulfane 
• 105456-43-7 sodium 2-(p-toluenesulfonylthio)ethanesulfinate 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 76339-61-2 Benzoesaeure-fluorsulfonsaeureanhydrid 

Downstream Products

• 1235-89-8 bis-(4-methyl-3-nitro-phenyl)-sulfone 
• 2449-35-6 bis(4-carboxyphenyl)sulfone 
• 4542-76-1 1-(4-(bromomethyl)phenylsulfonyl)-4-(bromomethyl)benzene 
• 34546-32-2 4,4'-sulfonyl-bis-toluene-2-sulfonyl chloride 
• 51347-00-3 1,1-Diphenyl-2-[4-(toluene-4-sulfonyl)-phenyl]-ethanol 
• 4423-10-3 4-(p-tolyl)pyridine 
• 4467-06-5 2-(4-methylphenyl)pyridine 
• 4423-09-0 4-(3-pyridyl)toluene 
• 55154-19-3 4,4'-sulfonyldibenzyl chloride 
• 16426-12-3 4-(p-Tolylsulfonyl)-dibenzyl 
• 620-94-0 di-(p-tolyl)sulfane 
• 106-44-5 p-cresol 
• 92-52-4 biphenyl 
• 861224-36-4 di{4-[(2-carboxyphenyloxy)methyl]phenyl}sulfone 

Relevant academic research and scientific papers

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

Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide

A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.

Synergistic cooperative effect of CF3SO2Na and bis(2-butoxyethyl)ether towards selective oxygenation of sulfides with molecular oxygen under visible-light irradiation

A safe, practical and eco-friendly method for the switchable synthesis of sulfoxides and sulfones through visible-light-initiated oxygenation of sulfides at ambient temperature under transition-metal-, additives-free and minimal solvent conditions. The synergistic catalytic efforts between CF3SO2Na and 2-butoxyethyl ether represents the key promoting factor for the reaction. This journal is

Electrochemical oxygenation of sulfides with molecular oxygen or water: Switchable preparation of sulfoxides and sulfones

A practical and eco-friendly method for the controllable aerobic oxygenation of sulfides by electrochemical catalysis was developed. The switchable preparation of sulfoxides and sulfones was effectively controlled by reaction time, in which both molecular oxygen and water can be used as the oxygen source under catalyst and external oxidant-free conditions. The electrochemical protocol features a broad substrate scope and excellent site selectivity and is successfully applied to the modification of some sulfide-containing pharmaceuticals and their derivatives. This journal is

Synthesis, spectra (FT-IR, NMR) investigations, DFT, FMO, MEP, NBO analysis and catalytic activity of MoO2(VI) complex with ONO tridentate hydrazone Schiff base ligand

A new dioxomolybdenum(VI) complex has been successfully prepared by the reaction of an ONO donor Schiff base, derived by condensing 4-amino-2-hydroxybenzohydrazide and 3-ethoxysalicylaldehyde, with MoO2(acac)2. The structures of synthesized products were explored spectroscopically through FT-IR, 1H & 13C NMR and by elemental composition (CHN) through combustion analysis. The tridentate Schiff base ligand is bonded to the central metal through its deprotonated enolic and phenolic oxygen atoms and by the nitrogen of the azomethine group. The interpretation of the data obtained through diffraction analysis validates the distorted octahedral geometry for the prepared metal complex. Furthermore, the catalytic potential of the molybdenum complex was explored for the selective oxidation of the aryl and alkyl sulfides to the corresponding sulfones in the presence of 30% aqueous H2O2 in ethanol. The main edge of the present catalytic work is the accomplishment of reaction in a short period of time, high percentage yield and easy work-up procedure.

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.

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.

Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis

An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.

Visible-light-driven electron donor-acceptor complex induced sulfonylation of diazonium salts with sulfinates

This work reports an efficient sulfonylation reaction enabled by a visible-light-induced radical coupling reaction between phenyl/heterocyclic diazonium salts and sulfinates. Mechanistic experiments disclosed the formation of a versatile electron donor-acceptor (EDA) complex. This transformation is characterized by an easy operational procedure under mild conditions which avoids transition metals, ligands, catalysts, and oxidants.

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.