172338-47-5

Basic information

• Product Name: Benzene, 1-chloro-2-[(S)-methylsulfinyl]-
• CAS NO: 172338-47-5
• Molecular Formula: C7H7ClOS
• Molecular Weight: 174.651
• Mol File: 172338-47-5.mol
• Article Data: 27

Chemical Properties

• CAS DataBase Reference: Benzene, 1-chloro-2-[(S)-methylsulfinyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-chloro-2-[(S)-methylsulfinyl]-(172338-47-5)
• EPA Substance Registry System: Benzene, 1-chloro-2-[(S)-methylsulfinyl]-(172338-47-5)

Safety Data

• Hazardous Substances Data: 172338-47-5(Hazardous Substances Data)

Upstream product

• 917-64-6 methyl magnesium iodide 
• 243143-03-5 (SS,1R,2S,5R)-(-)-1-(2-chlorophenylsulfinyloxy)-2-isopropyl-5-methylcyclohaxane 
• 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 
• 17733-22-1 2-chlorothioanisole 
• 164021-74-3 (1S,2R)-(-)-2-[N-(3’,5’-di-tert-butylsalicylidene)amino]-1,2-diphenylethanol 
• 95-51-2 o-chloroaniline 
• 45750-59-2 2-chlorobenzenesulphinic acid 

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.

Chiral: N, N ′-dioxide-iron(iii)-catalyzed asymmetric sulfoxidation with hydrogen peroxide

A highly enantioselective sulfoxidation of various sulfides has been achieved by a N,N′-dioxide-iron(iii) complex with 35% aq. H2O2 as the oxidant. The utility of the current method was demonstrated by asymmetric gram-scale synthesis of drug molecule (R)-modafinil. Moreover, a possible working mode was provided to elucidate the chiral induction.

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.