4850-73-1

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 2-(METHYLSULFINYL)BENZENECARBOXYLATE is used as an active pharmaceutical ingredient for its potential antioxidant and anti-inflammatory properties, which may contribute to the treatment of various medical conditions.
Used in Food Additive Industry:
In the food additive industry, METHYL 2-(METHYLSULFINYL)BENZENECARBOXYLATE is used as a preservative or flavor enhancer, leveraging its natural occurrence and potential health benefits.
Used in Research Applications:
METHYL 2-(METHYLSULFINYL)BENZENECARBOXYLATE is utilized as a research compound for studying its potential role in medical treatments and for understanding its antioxidant and anti-inflammatory mechanisms of action.

InChI:InChI=1/C9H10O3S/c1-12-9(10)7-5-3-4-6-8(7)13(2)11/h3-6H,1-2H3

Upstream product

• 144-86-5 N-chloro-4-methylbenzenesulfonamide 
• 3704-28-7 methyl 2-(methylthio)benzoate 
• 4892-02-8 Methyl thiosalicylate 
• 75-16-1 methylmagnesium bromide 
• 67-68-5 dimethyl sulfoxide 
• 134-20-3 2-carbomethoxyaniline 
• 186581-53-3 diazomethane 
• 19093-34-6 2-(methylsulfinyl)benzoic acid 

Downstream Products

• 3704-28-7 methyl 2-(methylthio)benzoate 
• 16605-99-5 biphenyl-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Diastereoselective oxidation of menthyl arenesulfenates to sulfinates and access to enantioenriched aryl methyl sulfoxides

Three aryl methyl sulfoxides were prepared via the following sequence: synthesis of the menthyl arenesulfenate from the corresponding thiol, diastereoselective oxidation leading to the sulfinate, then reaction with a Grignard reagent. The aryl moiety was substituted with a methyl ester on the ortho position or a nitro group on the ortho or the para position. The sulfenate esters were obtained in fair to excellent yield (42–82%). Four different oxidizing agents were tested to obtain the corresponding sulfinate esters with diastereomeric excesses (de) ranging from 10 to 48%. After separation of the diastereomers and reaction with methyl Grignard reagent, two enantiopure sulfoxides and one enantioenriched sulfoxide (32% ee) were obtained.

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.

On-Demand Generation and Use in Continuous Synthesis of the Ambiphilic Nitrogen Source Chloramine

Herein, we demonstrate the on-demand synthesis of chloramine from aqueous ammonia and sodium hypochlorite solutions, and its subsequent utilization as an ambiphilic nitrogen source in continuous-flow synthesis. Despite its advantages in cost and atom economy, chloramine has not seen widespread use in batch synthesis due to its unstable and hazardous nature. Continuous-flow chemistry, however, provides an excellent platform for generating and handling chloramine in a safe, reliable, and inexpensive manner. Unsaturated aldehydes are converted to valuable aziridines and nitriles, and thioethers are converted to sulfoxides, in moderate to good yields and exceedingly short reaction times. In this telescoped process, chloramine is generated in situ and immediately used, providing safe and efficient conditions for reaction scale-up while mitigating the issue of its decomposition over time.

Electrochemical synthesis of methyl sulfoxides from thiophenols/thiols and dimethyl sulfoxide

A new route for a one-pot synthesis of methyl sulfoxides from thiophenols/thiols and dimethyl sulfoxide using an electrochemical technique was developed. This protocol proceeded smoothly by employing electrons and hydrogen peroxide as clean oxidants, and a wide range of aromatic and aliphatic sulfoxides were synthesized in moderate to good yields.

Method for preparing chiral sulfoxide through catalysis of asymmetric oxidation of thioether

The invention provides a method for preparing chiral sulfoxide. According to the method, in a mixed solvent, thioether is used as a substrate, a complex produced by chiral tetradentate organic ligand and a metal manganese compound in situ is used as a cat

Visible light catalyzed methylsulfoxidation of (het)aryl diazonium salts using DMSO

The visible light catalyzed methylsulfoxidation of (het)aryl diazonium salts using DMSO is illustrated. This is the first example of DMSO being used as the source of the methylsulfinyl group. The procedure tolerates a wide range of functional groups on (het)aryl diazonium salts and provides aryl methyl sulfoxides in excellent yields under mild reaction conditions.

Preparation, Characterization, and Oxygenase Activity of a Photocatalytic Artificial Enzyme

A bicyclo[6,1,0]nonyne-substituted 9-mesityl-10-methyl-acridinium cofactor was prepared and covalently linked to a prolyl oligopeptidase scaffold containing a genetically encoded 4-azido-L-phenylalanine residue in its active site. The resulting artificial

Enantioselective oxidation of sulfides with H2O2 catalyzed by a pre-formed manganese complex

A facile and environmentally friendly method is presented for the asymmetric oxidation of sulfides with H2O2, utilizing a pre-formed manganese complex. Just in the presence of a low catalytic amount of carboxylic acid (CA), a variety of sulfide substrates, including aryl alkyl, aryl benzyl and cyclic sulfides, reacted to form chiral sulfoxides in high yields (up to 95%) and excellent enantioselectivities (>99% ee) under mild conditions. Moreover, the practical utility of the method has been demonstrated by the synthesis of esomeprazole and albendazole sulfoxide (ABZO).

Oxidation of organic sulfides by imidazolium fluorochromate: A kinetic and mechanistic approach

The oxidation of organic sulfides by imidazolium fluorochromate resulted in the formation of the corresponding sulfoxides. The reaction is first order with respect to imidazolium fluorochromate. A Michaelis-Menten type kinetics was observed with respect t

Oxidation of organic sulfides by tetraethylammonium chlorochromate: A kinetic and mechanistic study

The oxidation of organic sulfides by tetraethylammonium chlorochromate (TEACC) resulted in the formation of the corresponding sulfoxides. The reaction is first order with respect to both TEACC and the sulfide. The reaction is catalyzed by toluene-p-sulfon