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Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
(R)-1-bromo-3-(methylsulfinyl)benzene is utilized as a building block in the preparation of various pharmaceuticals and agrochemicals. Its unique structure allows for the creation of a wide range of biologically active molecules, making it a valuable asset in the development of new drugs and agricultural products.
Used in Organic Synthesis as a Reagent:
(R)-1-bromo-3-(methylsulfinyl)benzene serves as a reagent for the synthesis of chiral sulfoxides and sulfides, which are important structural motifs in many biologically active molecules. The presence of the chiral center in (R)-1-bromo-3-(methylsulfinyl)benzene enables the production of enantiomerically pure compounds, which is crucial for the effectiveness and safety of pharmaceuticals.
Used in the Development of New Materials:
(R)-1-bromo-3-(methylsulfinyl)benzene has potential applications in the development of new materials, thanks to its unique chemical properties and reactivity. This makes it a promising candidate for research and innovation in material science.
Used as a Precursor for Chiral Ligands in Asymmetric Catalysis:
In the field of organic synthesis, (R)-1-bromo-3-(methylsulfinyl)benzene is also used as a precursor for the preparation of chiral ligands for asymmetric catalysis. These ligands play a vital role in enhancing the selectivity and efficiency of various chemical reactions, leading to the production of enantiomerically enriched products.

Upstream product

• 33733-73-2 3-bromo-1-(methylthio)benzene 
• 29959-92-0 1-bromo-3-methanesulfinyl-benzene 

Relevant academic research and scientific papers

Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes

Several novel binaphthyl-based chiral hypervalent iodine(III) reagents have been prepared and structurally analysed. Various asymmetric oxidative reactions were applied to evaluate the reactivities and stereoselectivities of those reagents. Moderate to excellent yields were observed; however, very low stereoselectivities were obtained. NMR experiments indicated that these reagents are very easily hydrolysed in either chloroform or DMSO solvents leading to the limited stereoselectivities. It is concluded that the use of chiral ligands is an unsuccessful way to prepare efficient stereoselective iodine(III) reagents.

Two enantiocomplementary Baeyer-Villiger monooxygenases newly identified for asymmetric oxyfunctionalization of thioether

Two enantiocomplementary Baeyer-Villiger monooxygenases RaBVMO and AmBVMO were identified by genome mining for the asymmetric sulfoxidation. Both recombinant BVMOs have optimal pH of 9.0 and temperature of 35 °C. The half-lives of RaBVMO and AmBVMO at 30 °C were 24.4 and 24.6 h. RaBVMO and AmBVMO exhibited broad substrate spectrum and could catalyze the oxidization of various compounds including fatty ketones, cyclic ketones, and thioethers. Kinetic parameters analysis revealed that both RaBVMO and AmBVMO displayed higher catalytic efficiency toward thioanisole than cyclohexanone. As much as 50 mM thioanisole could be completely oxidized by AmBVMO and RaBVMO with 99% (R) and 95% (S), respectively. Molecular docking analysis further provides evidence for the complementary enantioselectivity of RaBVMO and AmBVMO. Our results demonstrate the potential application of the two novel BVMOs in asymmetric synthesis of sulfoxides.

Stereoselective sulfoxidation catalyzed by achiral Schiff base complexes in the presence of serum albumin in aqueous media

Four coordination complexes ML derived from an achiral Schiff base ligand (H2L = 2,2′-[(1,2-ethanediyl)bis(nitrilopropylidyne)]bisphenol) have been synthesized and characterized. A method is described for the enantioselective oxidation of a series of aryl alkyl sulfides using the coordination complexes in the presence of serum albumins (SAs) in an aqueous medium at ambient temperature. The mixture of metal complexes with serum albumins is useful for inducing asymmetric catalysis. The complex, albumin source and substrate influence stereoselective sulfoxidation. At optimal pH with the appropriate oxidant, some of ML/SA systems are identified as very efficient catalysts, giving the corresponding sulfoxides in excellent chemical yield (up to 100%) and good enantioselectivity (up to 94% ee) in certain cases. UV–visible spectroscopic data provide evidence that stronger binding between the complex and serum albumin lead to higher enantioselectivity.

HPLC enantioseparation on a homochiral MOF-silica composite as a novel chiral stationary phase

The last frontier in the development of chiral stationary phases for chromatographic enantioseparation involves homochiral metal-organic frameworks (MOFs). Using enantiopure (R)-2,2′-dihydroxy-1,1′-binaphthalene-6,6′-dicarboxylic acid as a starting material, we prepared three homochiral MOFs that were further used as chiral stationary phases for high-performance liquid chromatography to separate the enantiomers of various kinds of racemic sulfoxides, sec-alcohols, β-lactams, benzoins, flavanones and epoxides. The experimental results showed excellent performances for enantioseparation, and highlighted that enantioseparation on homochiral MOF columns is practical.

Efficient HPLC enantiomer separation using a pillared homochiral metal-organic framework as a novel chiral stationary phase

HPLC enantioseparation of racemates using novel pillared homochiral metal-organic framework-silica composite as chiral stationary phase has been successfully demonstrated.

Asymmetric catalytic sulfoxidation by a novel v IV 8 cluster catalyst in the presence of serum albumin: A simple and green oxidation system

A novel VIV8 cluster formulated as [V8O12(OH)4(CH3O)4(DAC)4]·7CH3OH (1) (DAC = 1,2-diaminocyclohexane) has been constructed successfully. Enantioselective oxidation of a series of alkyl aryl sulfides catalyzed by 1 is tested in an aqueous medium in the presence of serum albumin. The catalytic procedure is found to be simple and environmentally friendly. The influences of the parameters such as concentration of catalyst and oxidant, pH, and reaction time on the thioanisole as models are investigated. Under optimum conditions, 1 exhibits high conversion (up to 99%), excellent chemoselectivity (≥90% in all cases) and moderate enantioselectivity (up to 75% ee). After binding with serum albumin, the catalytic activity of 1 is promoted. The bovine serum albumin (BSA) and pig serum albumin (PSA) molecules have a more positive effect on the catalytic activity.

Development of a Continuous-Flow Microreactor for Asymmetric Sulfoxidation Using a Biomimetic Manganese Catalyst

Asymmetric sulfoxidation catalyzed by a biomimetic manganese complex under continuous-flow microreactor is described. The reaction is conducted in microreactor, it can rapidly (4 min) oxidize a wide scope of sulfides with high yield (up to 91%) and excel

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

Bovine serum albumin-cobalt(II) Schiff base complex hybrid: An efficient artificial metalloenzyme for enantioselective sulfoxidation using hydrogen peroxide

An artificial metalloenzyme (BSA-CoL) based on the incorporation of a cobalt(ii) Schiff base complex {CoL, H2L = 2,2′-[(1,2-ethanediyl)bis(nitrilopropylidyne)]bisphenol} with bovine serum albumin (BSA) has been synthesized and characterized. Attention is focused on the catalytic activity of this artificial metalloenzyme for enantioselective oxidation of a variety of sulfides with H2O2. The influences of parameters such as pH, temperature, and the concentration of catalyst and oxidant on thioanisole as a model are investigated. Under optimum conditions, BSA-CoL as a hybrid biocatalyst is efficient for the enantioselective oxidation of a series of sulfides, producing the corresponding sulfoxides with excellent conversion (up to 100%), chemoselectivity (up to 100%) and good enantiomeric purity (up to 87% ee) in certain cases.

Bimetallic titanium complex catalyzed enantioselective oxidation of thioethers using aqueous H2O2 as a terminal oxidant

A series of dimeric amino alcohol derived Schiff bases with various chiral amino alcohols and their corresponding bimetallic titanium complex were generated in situ. Thereafter with the in situ generated complexes, the asymmetric oxidation of prochiral aryl alkyl sulfides has been investigated using aqueous H2O2 as a terminal oxidant. During the study we found that the use of methanol or tert-butanol as an additive improved the catalytic activity in terms of both conversion and enantioselectivity. Moreover we observed a co-operative effect of the two reactive units of the bimetallic complex, which results in high reactivity as well as enantioselectivity compared to the corresponding monomeric complex. With this improved catalytic system several aryl alkyl sulfides and 1,3-dithianes were oxidised to the corresponding sulfoxides with good to high enantioselectivity (ee 78-99%) and conversion (70-99%). Unlike the monomer, oxidation of substrates like benzyl phenyl sulfide was achieved with high enantioselectivity as well as high yield.