20268-16-0

Basic information

• Product Name: (R)-(+)-2-chlorophenyl 4-methylphenyl sulfoxide
• Synonyms: (R)-(+)-2-chlorophenyl 4-methylphenyl sulfoxide
• CAS NO: 20268-16-0
• Molecular Weight: 250.749
• Mol File: 20268-16-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R)-(+)-2-chlorophenyl 4-methylphenyl sulfoxide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2-chlorophenyl 4-methylphenyl sulfoxide(20268-16-0)
• EPA Substance Registry System: (R)-(+)-2-chlorophenyl 4-methylphenyl sulfoxide(20268-16-0)

Safety Data

• Hazardous Substances Data: 20268-16-0(Hazardous Substances Data)

Upstream product

• 95-51-2 o-chloroaniline 
• 45750-59-2 2-chlorobenzenesulphinic acid 
• 6749-78-6 4-methylphenylmagnesium iodide 
• 243143-03-5 (SS,1R,2S,5R)-(-)-1-(2-chlorophenylsulfinyloxy)-2-isopropyl-5-methylcyclohaxane 
• 36692-27-0 2-chlorophenylmagnesium bromide 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 

Downstream Products

• 20608-65-5 (+/-)-2-chlorophenyl 4-methylphenyl sulfoxide 
• 135145-21-0 (S)-1-[3-Chloro-2-((S)-toluene-4-sulfinyl)-phenyl]-ethanol 
• 135145-20-9 (R)-1-[3-Chloro-2-((S)-toluene-4-sulfinyl)-phenyl]-ethanol 
• 135145-30-1 [3-Chloro-2-((S)-toluene-4-sulfinyl)-phenyl]-(4-methoxy-phenyl)-methanol 
• 135145-26-5 [3-Chloro-2-((S)-toluene-4-sulfinyl)-phenyl]-phenyl-methanol 
• 135145-28-7 [3-Chloro-2-((S)-toluene-4-sulfinyl)-phenyl]-p-tolyl-methanol 
• 49833-45-6 tert-butyl 4-methylphenyl sulfoxide 
• 62961-00-6 (S)-1-(ethylsulfinyl)-4-methylbenzene 
• 30506-35-5 butyl(p-tolyl)sulfoxide 
• 120121-01-9 (R)-1-(3-chlorophenyl)-ethanol 
• 135145-34-5 (S)-1-(m-chlorophenyl)ethanol 
• 135145-35-6 (3-chlorophenyl)(p-tolyl)methanol 

Relevant articles and documents

Preparation of optically active ortho-chloro- and ortho-bromophenyl sulfoxides

The preparation of the diastereomerically pure menthyl (S)-2-chloro- and (S)-2-bromophenyl sulfinates by esterification of the corresponding sulfinic acids with (1R,2S,5R)-(-)-menthol and recrystallization/epimerization is reported. The two sulfinates have been converted into enantiomerically pure aryl, vinyl and alkyl sulfoxides by reaction with organomagnesium reagents. These sulfoxides are useful chiral auxiliaries to control the stereochemical outcome of radical reactions.

Extremely Facile Ligand-Exchange and Disproportionation Reactions of Diaryl Sulfoxides, Selenoxides, and Triarylphosphine Oxides with Organolithium and Grignard Reagents

Diaryl sulfoxides undergo unusually rapid ligand-exchange reaction upon treatment with organolithium reagents at -95 deg C.Optically pure phenyl p-tolyl sulfoxide (4b) reacted with organolithium reagents at the range from -20 to -95 deg C to give facile ligand-exchange and disproportionation products, i.e., diphenyl sulfoxide (7), recovered 4b, and di-p-tolyl sulfoxide (8) in a statistical ratio of 1:2:1 in quantitative yields, and the recovered 4b was completely racemized.This facile ligand exchange was observed in the similar reactions using only diaryl selenoxides and triarylphosphine oxides.The reactions of 18O-labeled phenyl p-tolyl sulfoxide (4c) with organolithium reagents gave products in a statistical ration without 18O scrambling, indicating that only the C-S bond cleavage took place under low temperature.It is suggested that the ligand exchange reactions occur by the nucleophilic attack by organolithium reagent at the sulfinyl sulfur atom, giving ?-sulfurane as an intermediate that collapses rapidly.These results suggest that the treatment of arylic sulfoxides, selenoxides, and phosphine oxides with strong bases should be effected with caution.