4820-08-0

Basic information

• Product Name: Benzene, 1-methyl-4-[(phenylmethyl)sulfinyl]-, (S)-
• CAS NO: 4820-08-0
• Molecular Formula: C14H14OS
• Molecular Weight: 230.331
• Mol File: 4820-08-0.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1-methyl-4-[(phenylmethyl)sulfinyl]-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-methyl-4-[(phenylmethyl)sulfinyl]-, (S)-(4820-08-0)
• EPA Substance Registry System: Benzene, 1-methyl-4-[(phenylmethyl)sulfinyl]-, (S)-(4820-08-0)

Safety Data

• Hazardous Substances Data: 4820-08-0(Hazardous Substances Data)

Upstream product

• 100-53-8 phenylmethanethiol 
• 921765-53-9 3-(phenylmethylsulfinyl)propionic acid tert-butyl ester 
• 624-31-7 4-tolyl iodide 
• 106-45-6 para-thiocresol 
• 104-15-4 toluene-4-sulfonic acid 
• 100-44-7 benzyl chloride 
• 5023-60-9 1-benzylsulfanyl-4-methyl-benzene 
• 32018-21-6 2-[(4-methylphenyl)sulfanyl]ethyl phenyl sulfone 
• 1308833-65-9 1-methyl-4-[(2-(phenylsulfonyl)ethyl)sulfinyl]benzene 
• 100-39-0 benzyl bromide 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 10381-70-1 benzyl 4-methylphenyl sulfoxide 
• 31350-96-6 (S)-1-(bromomethylsulfinyl)-4-methylbenzene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 86448-74-0 (R)-1,2-Diphenyl-2-((S)-toluene-4-sulfinyl)-ethanone 
• 184636-31-5 (R)-2-Ethoxycarbonylamino-3,3,3-trifluoro-2-[(R)-phenyl-((R)-toluene-4-sulfinyl)-methyl]-propionic acid methyl ester 
• 184636-30-4 (S)-2-Ethoxycarbonylamino-3,3,3-trifluoro-2-[(R)-phenyl-((R)-toluene-4-sulfinyl)-methyl]-propionic acid methyl ester 
• 49833-45-6 tert-butyl 4-methylphenyl sulfoxide 
• 86448-79-5 (1S,2R)-1,2-Diphenyl-2-((S)-toluene-4-sulfinyl)-ethanol 
• 104891-20-5 (S)-3-Bromo-1-phenyl-1-((R)-toluene-4-sulfinyl)-propan-2-one 
• 104891-16-9 (S)-3-Chloro-1-phenyl-1-((R)-toluene-4-sulfinyl)-propan-2-one 
• 109958-04-5 (4S)-2-methylene-4-phenyl-γ-butyrolactone 
• 100907-29-7 (R)-2-Methylene-4-phenyl-4-p-tolylsulfanyl-butyric acid 
• 158560-34-0 (2S,2'R,R_S)-2-fluoromethyl-2-<<(4-methylphenyl)sulfinyl>methyl>oxirane 
• 158560-41-9 (S)-2-benzyl-3-fluoro-1-<(N-trifluoroacetyl)benzylamino>propan-2-ol 
• 184636-43-9 (S)-2-Benzyloxycarbonylamino-3,3,3-trifluoro-2-((R)-phenyl-p-tolylsulfanyl-methyl)-propionic acid methyl ester 

Relevant articles and documents

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.

Localized Partitioning of Enantiomers in Solid Samples of Sulfoxides: Importance of Sampling Method in Determination of Enantiopurity

Localized partitioning of amorphous enantioenriched aryl benzyl sulfoxides in the solid state can lead to substantial variation in enantiopurities, even for sulfoxides which do not show detectable levels of self-disproportionation of enantiomers (SDE) dur

Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications

Herein we reported an efficient palladium-catalyzed enantioselective arylation of both alkyl and aryl sulfenate anions to deliver various chiral sulfoxides in good yields (up to 98%) with excellent enantioselectivities (up to 99% ee) by the use of our developed chiral O,P-ligands (PC-Phos). PC-Phos are easily prepared in short steps from inexpensive commercially available starting materials. The single-crystal structure of the PC4/PdCl2 showed that a rarely observed 11-membered ring was formed via the O,P-coordination with the palladium(II) center. The salient features of this method include general substrate scope, ease of scale-up, applicable to the late-stage modification of bioactive compounds, and the synthesis of a marketed medicine Sulindac.

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

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

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).

Investigation of steric and electronic effects in the copper-catalysed asymmetric oxidation of sulfides

Steric and electronic effects in the copper-catalysed asymmetric oxidation of aryl benzyl, aryl alkyl and alkyl benzyl sulfides have been investigated. The presence of an aryl group directly attached to the sulfur is essential to afford sulfoxides with high enantioselectivities, with up to 97% ee for 2-naphthyl benzyl sulfoxide, the highest enantioselectivity achieved to date for copper-catalysed asymmetric sulfoxidation. In contrast, the benzyl substituent can be replaced by sterically comparable groups with no effect on enantioselectivity. Copper-mediated oxidation of substituted aryl benzyl sulfides display modest steric and electronic effects resulting in comparable or lower enantioselectivities to those obtained with the unsubstituted benzyl phenyl sulfide.

Asymmetric oxidation catalysis by a porphyrin-inspired manganese complex: Highly enantioselective sulfoxidation with a wide substrate scope

The first genuinely promising porphyrin-inspired manganese-catalyzed asymmetric sulfoxidation method using hydrogen peroxide has been successfully developed, allowing for rapidly oxidizing (0.5-1.0 h) a wide variety of sulfides in high yields with excellent enantioselectivities (up to >99% ee).

Copper-catalyzed asymmetric oxidation of sulfides

Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of th

A new methodology for the oxidation of sulfides with Fe(III) catalysts

A variety of sulfides were converted to the corresponding sulfoxide derivatives with 70% t-BuOOH (water) as the oxidant in the presence of catalytic quantity of Fe2(SO4)3. The method described has a wide range of applicati