4850-71-9

Basic information

• Product Name: Benzene, [(R)-methylsulfinyl]-
• CAS NO: 4850-71-9
• Molecular Formula: C7H8OS
• Molecular Weight: 140.206
• Mol File: 4850-71-9.mol
• Article Data: 245

Chemical Properties

• CAS DataBase Reference: Benzene, [(R)-methylsulfinyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [(R)-methylsulfinyl]-(4850-71-9)
• EPA Substance Registry System: Benzene, [(R)-methylsulfinyl]-(4850-71-9)

Safety Data

• Hazardous Substances Data: 4850-71-9(Hazardous Substances Data)

Upstream product

• 3071-32-7 1-phenylethyl hydroperoxide 
• 100-68-5 methyl-phenyl-thioether 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 66021-66-7 p-TolSO₂NO 
• 60933-65-5 (R)-S-methyl-S-phenylsulfoximine 
• 100-59-4 phenylmagnesium chloride 
• 142635-35-6 (4S)-4-benzyl-3-<(S)-methylsulfinyl>-2-isoxazolidinone 
• 917-54-4 methyllithium 
• 77382-90-2 (S)-o-<1-((S)-1-α-naphtylethylamino)ethyl>phenol 
• 42843-29-8 Methanesulfinic acid (R)-((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 591-51-5 phenyllithium 
• 78347-75-8 N-<(S)-1-(o-hydroxyphenyl)ethyl>-N-<(S)-1-α-naphthylethyl> (S^R)-methylsulfinamide 
• 114026-76-5 (-)-(2R,3R)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[4.5]decane 
• 135802-77-6 (S_S)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl methanesulfinate 

Downstream Products

• 4381-25-3 (S)-S-methyl-S-phenylsulfoximine 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 560087-80-1 (S)-ethyl 2-(phenylsulfinyl)acetate 
• 1052719-06-8 C₁₆H₂₂O₂S 
• 1224430-90-3 C₁₄H₂₁NO₂S₂ 
• 1316846-42-0 C₂₁H₃₈O₇SSi 
• 1316846-43-1 C₂₁H₃₆O₇SSi 
• 1316846-45-3 C₂₇H₄₉NO₇S₂Si 
• 1316846-47-5 C₂₅H₄₃NO₇SSi 
• 1316846-48-6 C₂₄H₄₃NO₈SSi 
• 1316846-49-7 C₂₂H₂₉NO₁₀S 
• 1316846-50-0 C₂₈H₄₂O₆SSi 
• 1316846-35-1 C₁₉H₂₃BrO₅S 
• 1316846-38-4 C₁₉H₂₂O₅S 

Relevant articles and documents

Biocatalytic oxidation by chloroperoxidase from Caldariomyces fumago in polymersome nanoreactors

The encapsulation of chloroperoxidase from Caldariomyces fumago (CPO) in block copolymer polymersomes is reported. Fluorescence and electron microscopy show that when the encapsulating conditions favour self-assembly of the block copolymer, the enzyme is incorporated with concentrations that are 50 times higher than the enzyme concentration before encapsulation. The oxidation of two substrates by the encapsulated enzyme was studied: i) pyrogallol, a common substrate used to assay CPO enzymatic activity and ii) thioanisole, of which the product, (R)-methyl phenyl sulfoxide, is an important pharmaceutical intermediate. The CPO-loaded polymersomes showed distinct reactivity towards these substrates. While the oxidation of pyrogallol was limited by diffusion of the substrate into the polymersome, the rate-limiting step for the oxidation of thioansiole was the turnover by the enzyme.

Enantioselective Sulfoxidation of Thioanisole by Cascading a Choline Oxidase and a Peroxygenase in the Presence of Natural Deep Eutectic Solvents

A bienzymatic cascade for selective sulfoxidation is presented. The evolved recombinant peroxygenase from Agrocybe aegeritra catalyses the enantioselective sulfoxidation of thioanisole whereas the choline oxidase from Arthrobacter nicotianae provides the

Application of various ionic liquids as cosolvents for chloroperoxidase- catalysed biotransformations

Chloroperoxidase from Caldariomyces fumago catalyses oxidation of indole and thioanisole in reaction mixtures containing up to 40% (v/v) of different ionic liquids (ILs). Results indicate that ILs containing tosylate, trifluoroacetate, chloride, and methylsulfate anions are suitable cosolvents for these transformations, yielding high enantiomeric excess and good conversion rates.

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.

Efficient Synthesis of Sulfur-Stereogenic Sulfoximines via Ru(II)-Catalyzed Enantioselective C-H Functionalization Enabled by Chiral Carboxylic Acid

Ru(II)-catalyzed enantioselective C-H functionalization involving an enantiodetermining C-H cleavage step remains undeveloped. Here we describe a Ru(II)-catalyzed enantioselective C-H activation/annulation of sulfoximines with α-carbonyl sulfoxonium ylides using a novel class of chiral binaphthyl monocarboxylic acids as chiral ligands, which can be easily and modularly prepared from 1,1′-binaphthyl-2,2′-dicarboxylic acid. A broad range of sulfur-stereogenic sulfoximines were prepared in high yields with excellent enantioselectivities (up to 99% yield and 99% ee) via desymmetrization, kinetic resolution, and parallel kinetic resolution. Furthermore, the resolution products can be easily transformed to chiral sulfoxides and key intermediates for kinase inhibitors.