14763-60-1

Usage

Uses

Used in Pharmaceutical Industry:
4-Methylsulfonylphenol is used as a reagent for the synthesis of pyrazolo[3,4-d]pyrimidine derivatives, which are known as GPR119 agonists. These agonists have potential applications in the treatment of type 2 diabetes and obesity by modulating glucose homeostasis and insulin secretion.
Additionally, 4-Methylsulfonylphenol is used as a reagent in the synthesis of novel 2-(pyridine-2-yl)-1H-benzimidazole derivatives. These derivatives act as potent glucokinase activators, which can be utilized in the development of therapies for type 2 diabetes by improving glucose metabolism and insulin sensitivity.

Reactions

The reaction of 4-(methylsulfonyl)phenol (17.2 g, 100.0 mmol) with p-Toluenesulfonic anhydride as outlined in the general procedure provided 4-(methylsulfonyl)phenyl 4-methylbenzenesulfonate (26.1 g, 81%).

InChI:InChI=1/C9H13NO2/c10-6-8(11)7-12-9-4-2-1-3-5-9/h1-5,8,11H,6-7,10H2

Upstream product

• 3517-90-6 p-anisyl methyl sulfone 
• 98-57-7 4-chlorophenyl methyl sulfone 
• 1073-72-9 4-hydroxythioanisole 
• 67-56-1 methanol 
• 67451-16-5 4-(methylsulfonyl)phenyl acetate 
• 106-41-2 4-bromo-phenol 
• 20277-69-4 sodium methansulfinate 
• 540-38-5 p-Iodophenol 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 98546-51-1 (4-thiomethoxyphenyl)boronic acid 
• 455-15-2 1-(methylsufonyl)-4-fluorobenzene 
• 616-38-6 carbonic acid dimethyl ester 
• 3466-32-8 4-bromoohenyl methyl sulfone 
• 50910-13-9 4-methylsulfanyl(methylcarbonyloxy)benzene 

Downstream Products

• 67451-16-5 4-(methylsulfonyl)phenyl acetate 
• 99186-51-3 1-(allyloxy)-4-(methylsulfonyl)benzene 
• 106590-36-7 3,5-dinitro-benzoic acid-(4-methanesulfonyl-phenyl ester) 
• 20951-17-1 2-Chloromethyl-4-methanesulfonyl-phenol 
• 14793-43-2 C₈H₇NO₆S₂ 
• 20951-33-1 2-Chloro-6-(4-methanesulfonyl-phenoxy)-benzonitrile 
• 28239-88-5 Thiophosphoric acid O-(2-ethoxy-1-methyl-ethyl) ester O'-ethyl ester O''-(4-methanesulfonyl-phenyl) ester 
• 28239-84-1 Thiophosphoric acid O-ethyl ester O'-(4-methanesulfonyl-phenyl) ester O''-(2-propoxy-ethyl) ester 
• 28239-90-9 Thiophosphoric acid O-ethyl ester O'-(4-methanesulfonyl-phenyl) ester O''-(2-methoxy-1-methoxymethyl-ethyl) ester 
• 41989-55-3 Isopropoxymethyl-phosphonothioic acid O-ethyl ester O-(4-methanesulfonyl-phenyl) ester 
• 60962-96-1 1,3-Dibromo-2-(4-methanesulfonyl-phenoxy)-5-nitro-benzene 
• 58291-68-2 1,3-dichloro-2-(4-methanesulfonylphenoxy)-5-nitrobenzene 
• 20951-03-5 2,6-diiodo-4-methylsulfonylphenol 
• 20951-04-6 2,6-dibromo-4-methylsulfonylphenol 

Relevant academic research and scientific papers

A general copper-catalyzed sulfonylation of arylboronic acids

A general copper-catalyzed method for the sulfonylation of arylboronic acids with sulfinate salts is described. A variety of alkyl-aryl, diaryl, and alkyl-heteroaryl sulfones were synthesized in good yield.

Decarboxylative Hydroxylation of Benzoic Acids

Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.

COMPOSITES, METHODS AND USES THEREOF

The present invention relates, in general terms, to methods of catalysing a reaction, including the steps of contacting a chemical entity comprising a sulphide moiety with a composite and an oxidant. The composite acts as a heterogeneous catalyst to oxidise the sulphide moiety. The present invention also relates to composites, methods of synthesising the composites and its use as a catalyst thereof.

Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst

We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.

Radical-anion coupling through reagent design: hydroxylation of aryl halides

The design and development of an oxime-based hydroxylation reagent, which can chemoselectively convert aryl halides (X = F, Cl, Br, I) into phenols under operationally simple, transition-metal-free conditions is described. Key to the success of this approach was the identification of a reducing oxime anion which can interact and couple with open-shell aryl radicals. Experimental and computational studies support the proposed radical-nucleophilic substitution chain mechanism.

Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis

The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway.

Palladium-Catalyzed Hydroxylation of Aryl Halides with Boric Acid

Boric acid, B(OH)3, is proved to be an efficient hydroxide reagent in converting (hetero)aryl halides to the corresponding phenols with a Pd catalyst under mild conditions. Various phenol products were obtained in good to excellent yields. This transformation tolerates a broad range of functional groups and molecules, including base-sensitive substituents and complicated pharmaceutical (hetero)aryl halide molecules.

A practical method for preparation of phenols from arylboronic acids catalyzed by iodopovidone in aqueous medium

A novel and efficient strategy for the ipso-hydroxylation of arylboronic acids to phenols has been developed using inexpensive, readily available, air-stable water-soluble povidone iodine as catalyst and aqueous hydrogen peroxide as oxidizing agent. The reactions were performed at room temperature under metal-, ligand- and base-free condition in a short reaction time. The corresponding substituted phenols were obtained in moderate to good yields by oxidative hydroxylation of arylboronic acids in aqueous medium.

Photoinduced Hydroxylation of Organic Halides under Mild Conditions

Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.

Aryl Methyl Sulfone Construction from Eco-Friendly Inorganic Sulfur Dioxide and Methyl Reagents

A three-component cross-coupling protocol of boronic acid, sodium metabisulfite, and dimethyl carbonate was developed for the construction of significant functional methyl sulfones, in which introduction of sulfur dioxide at the last stage was successfully achieved in one step. Inorganic sodium metabisulfite was used as an eco-friendly sulfur dioxide source. Green dimethyl carbonate was employed as methyl reagent in this transformation. Diverse functional methyl sulfones were obtained from various readily available boronic acids. Notably, the last-stage modification of pharmaceuticals and the synthesis of Firocoxib were efficiently established through this strategy.