7321-57-5

Usage

Physical State

Colorless liquid

Odor

Slightly garlic-like

Uses

a. Intermediate in the synthesis of pharmaceuticals and agrochemicals
b. Production of dyes
c. Solvent for resins and polymers
d. Organic synthesis (preparation of sulfones and sulfides)

Health Risks

Potential hazards if not handled and used properly

Safety Precautions

Follow safety guidelines and procedures for handling and use

Upstream product

• 17733-22-1 2-chlorothioanisole 
• 139696-88-1 2-chlorophenyl methyl sulfoxide 
• 6320-03-2 2-chlorothiphenol 
• 1308834-12-9 2-[(2-chlorophenyl)sulfanyl]ethyl phenyl sulfone 
• 1308833-73-9 2-[(2-chlorophenyl)sulfinyl]ethyl phenyl sulfone 
• 74-88-4 methyl iodide 
• 92523-34-7 (2-chlorophenyl)(imino)(methyl)-λ⁶-sulfanone 
• 164021-74-3 (1S,2R)-(-)-2-[N-(3’,5’-di-tert-butylsalicylidene)amino]-1,2-diphenylethanol 
• 95-50-1 1,2-dichloro-benzene 
• 144-86-5 N-chloro-4-methylbenzenesulfonamide 

Downstream Products

• 64145-51-3 3-phenylcyclopentanone 
• 35515-26-5 1-Chloro-2-chloromethanesulfinyl-benzene 
• 38452-13-0 1-methylsulfinyl-2-methoxybenzene 
• 222961-69-5 [(R)-3-(2-Methanesulfinyl-phenoxy)-3-phenyl-propyl]-dimethyl-amine 
• 3079-27-4 methyl n-octylsulfoxide 
• 7321-57-5 (R)-(+)-o-chlorophenyl methyl sulfoxide 
• 172338-47-5 (R)-(+)-2-chlorophenyl methyl sulfoxide 
• 222961-71-9 Dimethyl-[(R)-3-(2-methylsulfanyl-phenoxy)-3-phenyl-propyl]-amine 
• 162938-15-0 (R)-N-methyl-3-(2-methylthiophenoxy)-3-phenyl-propylamine 
• 17733-22-1 2-chlorothioanisole 
• 92523-34-7 (2-chlorophenyl)(imino)(methyl)-λ⁶-sulfanone 
• 2457-37-6 1-chloro-2-thiocyanatobenzene 
• 1622424-65-0 3-(2-(3-chloro-2-(methylthio)phenyl)dodecanoyl)oxazolidin-2-one 

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.

Ligand Modification of Au25 Nanoclusters for Near-Infrared Photocatalytic Oxidative Functionalization

The inorganic-organic interface between metal catalysts and their substrates greatly influences reaction processes, but few studies of this interface have been conducted for a detailed understanding of its structure. Herein, we describe the synthesis and structural determination of an arylthiolated Au25(F-Ph)18- nanocluster and characterize in detail the key roles of its ligands in photocatalyzed oxidative functionalization reactions. The most significant findings are that (i) interactions are established between ligands to avoid distortion of the geometric structure, limit the Jahn-Teller effect, and protect the nanocluster from oxidization and (ii) the low energy gap (HOMO-LUMO) of the synthetic clusters enables three types of photocatalytic oxidative functionalization reactions by near-infrared light (850 nm).

Extending aromatic acids on TiO2 for cooperative photocatalysis with triethylamine: Violet light-induced selective aerobic oxidation of sulfides

Designing visible light photocatalysts with a metal oxide semiconductor as the starting material could expand a new horizon for the conversion and storage of solar energy. Here, the benchmark photocatalyst TiO2 was used to pursue this goal by a

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.

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.

Integrating hydrogen production with anodic selective oxidation of sulfides over a CoFe layered double hydroxide electrode

Replacing the sluggish oxygen evolution reaction (OER) with oxidation reactions for the synthesis of complex pharmaceutical molecules coupled with enhanced hydrogen evolution reaction (HER) is highly attractive, but it is rarely explored. Here, we report an electrochemical protocol for selective oxidation of sulfides to sulfoxides over a CoFe layered double hydroxide (CoFe-LDH) anode in an aqueous-MeCN electrolyte, coupled with 2-fold promoted cathodic H2productivity. This protocol displays high activity (85-96% yields), catalyst stability (10 cycles), and generality (12 examples) in selective sulfide oxidation. We demonstrate its applicability in the synthesis of four important pharmaceutical related sulfoxide compounds with scalability (up to 1.79 g). X-ray spectroscopy investigations reveal that the CoFe-LDH material evolved into amorphous CoFe-oxyhydroxide under catalytic conditions. This work may pave the way towards sustainable organic synthesis of valuable pharmaceuticals coupled with H2production.

Flow Electrosynthesis of Sulfoxides, Sulfones, and Sulfoximines without Supporting Electrolytes

An efficient electrochemical flow process for the selective oxidation of sulfides to sulfoxides and sulfones and of sulfoxides toN-cyanosulfoximines has been developed. In total, 69 examples of sulfoxides, sulfones, andN-cyanosulfoximines have been synthesized in good to excellent yields and with high current efficiencies. The synthesis was assisted and facilitated through a supporting electrolyte-free, fully automated electrochemical protocol that highlights the advantages of flow electrolysis.

Electrochemical Scalable Sulfoxidation of Sulfides with Molecular Oxygen and Water

An efficient and chemoselective synthesis of sulfoxides through the electrooxidation of sulfides has been well developed. This protocol takes advantage of electricity as the terminal oxidant and of molecular oxygen and water as the oxygen atom sources. A variety of structurally diverse sulfoxide compounds are assembled in moderate to excellent yields. The scaled-up reactions at 6–20 mmol show the good practicability and application potential of this methodology. A possible free radical mechanism has been proposed to rationalize the reaction procedure.

Bridging green light photocatalysis over hierarchical Nb2O5for the selective aerobic oxidation of sulfides

Nb2O5is a colourless metal oxide that is very promising in areas such as energy storage and optical glasses. These applications depend on the superior redox properties of Nb2O5compared to those of other metal ox