7321-58-6

Usage

Uses

Used in Organic Synthesis:
2-Bromophenylmethylsulfoxide is used as a reagent in organic synthesis for its ability to participate in copper-catalyzed coupling reactions, facilitating the formation of C-N and C-C bonds. This makes it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Development:
2-Bromophenylmethylsulfoxide is used as a potential drug candidate due to its demonstrated antioxidant and anti-inflammatory properties. Its potential in treating various diseases makes it a promising compound for further research and development in the pharmaceutical industry.
Used in Asymmetric Synthesis:
2-Bromophenylmethylsulfoxide is used in the preparation of chiral sulfoxides, which are essential for asymmetric synthesis. This application is crucial in the production of enantiomerically pure compounds, which are often required for biological activity and pharmaceutical applications.
Used in Research:
2-Bromophenylmethylsulfoxide is utilized in research settings to explore its properties and potential applications further. Its study contributes to the advancement of knowledge in organic chemistry and medicinal chemistry, paving the way for new discoveries and applications.

InChI:InChI=1S/C7H7BrOS/c1-10(9)7-5-3-2-4-6(7)8/h2-5H,1H3

Upstream product

• 19614-16-5 2-bromo-1-(methylsulfanyl)benzene 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 126218-83-5 1-bromo-2-(methylsulfinyl)benzene 
• 144-86-5 N-chloro-4-methylbenzenesulfonamide 
• 164021-74-3 (1S,2R)-(-)-2-[N-(3’,5’-di-tert-butylsalicylidene)amino]-1,2-diphenylethanol 
• 103053-00-5 2-bromobenzenesulfinyl chloride 
• 615-36-1 2-bromoaniline 
• 89581-50-0 ortho-bromobenzenesulfinic acid 
• 33733-73-2 3-bromo-1-(methylthio)benzene 
• 917-64-6 methyl magnesium iodide 
• 583-55-1 1-Bromo-2-iodobenzene 
• 6320-02-1 o-bromothiophenol 
• 67-68-5 dimethyl sulfoxide 

Downstream Products

• 573-57-9 1,4-dihydronaphthalene-1,4-epoxide 
• 1669-98-3 Ethyl methyl sulfoxide 
• 248954-04-3 3,7-bis[2-(methylsulfinyl)phenyl]dibenzothiophene 
• 33951-33-6 1-bromo-2-(methylsulfonyl)benzene 
• 7321-58-6 (S)-methyl o-bromophenyl sulfoxide 
• 7321-58-6 (R)-2-bromophenyl methyl sulfoxide 
• 1088098-07-0 2,7-bis[2-(methylsulfinyl)phenyl]-N-butyl-carbazole 
• 1231895-27-4 4-hexyl-2,6-bis[2-(methylsulfinyl)phenyl]-4H-dithieno[3,2-b:2',3'-d]pyrrole 
• 1231895-28-5 4,4-dihexyl-2,6-bis-2-(methylsulfinyl)phenylcyclopenta[2,1-b:3,4-b']dithiophene 
• 107344-54-7 1-<2-(Methylsulfinyl)phenyl>pyrrole 
• 241-34-9 benzo[1, 2-b: 4, 5-b']bis[b]benzothiophene 
• 222-24-2 benzo<2,1-b:3,4-b'>bisbenzothiophene 

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.

A Bimetallic Ag/Ti-Based Coordination Polymer as a Catalyst for Electrocatalytic CO2 Reduction and Selective Sulfide Oxidation

The first example of heterometallic Ag/Ti bimetallic-based coordination polymer was synthesized using salicylic acid as the ligand. The uniform Ag/Ti?O rod array has efficient electrocatalytic CO2 reduction activity with a Faradaic efficiency (FE) of 90.3 % at ?0.88 V (vs RHE) and a maximum TOF of 658 h?1 at ?1.08 V. The chemical catalytic property of the Ag/Ti?O rod was also studied, and the results showed that the Ag/Ti?O rod has good catalytic performance for selective oxidation of sulfide to sulfoxide.

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.

A μ-AsO4-Bridging Hexadecanuclear Ni-Substituted Polyoxotungstate

A novel tetrahedral μ-AsO4-bridging hexadecanuclear Ni-substituted silicotungstate (ST) Na21H10[(AsO4){Ni8(OH)6(H2O)2(CO3)2(A-α-SiW9O34)2}2]·60H2O (1) was made by the reactions of trivacant [A-α-SiW9O34]10- ({SiW9}) units with Ni2+ cations and Na3AsO4·12H2O and characterized by IR spectrometry, elemental analysis, thermogravimetric analysis (TGA), and powder X-ray diffraction (PXRD). 1 contains a novel polyoxoanion [(AsO4){Ni8(OH)6(H2O)2(CO3)2(A-α-SiW9O34)2}2]31- built by four trivacant Keggin [A-α-SiW9O34]10- fragments linked through an unprecedented [(AsO4){Ni8(OH)6(H2O)2(CO3)2}2]9+ cluster, where the tetrahedral AsO4 acts as an exclusively μ2-bridging unit to link multiple Ni centers; such a connection mode appears for the first time in polyoxometalate chemistry. Furthermore, the electrochemical and catalytic oxidation properties of compound 1 have been investigated.

A {Ti6W4}-Cluster-Substituted Polyoxotungstate: Synthesis, Structure, and Catalytic Oxidation Properties

A novel Ti-W-O-cluster-substituted tungstoantimonate (TA), [H2N(CH3)2]3Na4H9[{Ti6W4O18(OH)(H2O)3}(B-α-SbW9O33)3]·20H2O (1), has been made by hydrothermal reactions of trivacant [B-α-SbW9O33]9- units, Ti4+ cations, and WO42- anions in the presence of [H2N(CH3)2]·Cl and structurally characterized. Intriguingly, the polyoxoanion of 1 is constructed from three [B-α-SbW9O33]9- units and a previously unobserved decanuclear heterometallic Ti-W-O cluster [Ti6W4O18(OH)(H2O)3]11+ ({Ti6W4}) that is comprised of an octahedral [Ti6WO6(H2O)3]18+ cluster and an edge-sharing [W3O12(OH)]7- fragment via six W-O-Ti/W linkers. Furthermore, studies on the catalytic oxidation properties reveal that 1 possesses good catalytic activity toward the oxidation reactions of various sulfides and cyclooctene based on the environmentally friendly oxidant H2O2.

{Ti6}/{Ti10} Wheel Cluster Substituted Silicotungstate Aggregates

Two novel Ti-oxo wheel cluster substituted silicotungstates (STs) [H2N(CH3)2]9H9[Ti6O6(SiW10O37)3]·11H2O (1) and [H2N(CH3)2]16H10[Ti10O11(SiW10O37)2(SiW9O35)2]·14H2O (2) have been made by hydrothermal reactions. The polyoxoanion of 1 is a ring-shaped trimer where a Ti6O6 ({Ti6}) wheel cluster is encapsulated by three divacant [SiW10O37]10- (SiW10O37) fragments. However, 2 is built by two divacant SiW10O37 units and two rare trivacant [SiW9O35]12- (SiW9O35) fragments and further installs an unprecedented Ti10O11 ({Ti10}) double-wheel cluster. To the best of our knowledge, 2 is rare in POM chemistry. Studies on the catalytic oxidation properties reveal that 1 exhibits high catalytic activity toward the oxidation of various sulfides using H2O2 as an oxidant. Furthermore, 1 can be facilely recycled and reused for at least five cycles without obvious loss of catalytic activity.

Synthesis method of sulfoxide compound

The invention discloses a method for preparing sulfoxide derivatives with industrial application value through substituted diaryl (heterocyclic aryl) and aryl (heterocyclic aryl) alkyl sulfide compounds. Under electrochemical reaction conditions, diaryl (heterocyclic aryl) and aryl (heterocyclic aryl) alkyl sulfide compounds which are wide in source and easy to prepare and have structural diversity are used as raw materials, lithium perchlorate (LiClO4) is used as an electrolyte, acetonitrile (CH3CN) is used as a solvent, and oxygen is used as an oxidizing agent to prepare the diaryl (heterocyclic aryl) and aryl (heterocyclic aryl) alkyl sulfoxide derivatives. Compared with reported preparation methods of sulfoxide derivatives, the preparation method disclosed by the invention is green, environment-friendly, safe, energy-saving, wide in substrate application range, good in compatibility of product functional groups, easy in obtaining of raw materials and simple and convenient to operate.

Catalyst-free visible light-mediated selective oxidation of sulfides into sulfoxides under clean conditions

A facile and efficient visible-light-mediated method for directly converting sulfides into sulfoxides under clean conditions without using any photocatalysts is reported. This method exhibited favourable compatibility with functional groups and afforded a series of sulfoxides with high selectivity and yields. Moreover, in order to shed more light on such a transformation, detailed mechanism studies were carried out both experimentally and theoretically. The readily accessible, low-cost and eco-friendly nature of the developed method will endow it with attractive applications in chemical synthesis.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

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