243143-03-5

Basic information

• Product Name: (SS,1R,2S,5R)-(-)-1-(2-chlorophenylsulfinyloxy)-2-isopropyl-5-methylcyclohaxane
• CAS NO: 243143-03-5
• Molecular Weight: 314.876
• Mol File: 243143-03-5.mol

Chemical Properties

• CAS DataBase Reference: (SS,1R,2S,5R)-(-)-1-(2-chlorophenylsulfinyloxy)-2-isopropyl-5-methylcyclohaxane(CAS DataBase Reference)
• NIST Chemistry Reference: (SS,1R,2S,5R)-(-)-1-(2-chlorophenylsulfinyloxy)-2-isopropyl-5-methylcyclohaxane(243143-03-5)
• EPA Substance Registry System: (SS,1R,2S,5R)-(-)-1-(2-chlorophenylsulfinyloxy)-2-isopropyl-5-methylcyclohaxane(243143-03-5)

Safety Data

• Hazardous Substances Data: 243143-03-5(Hazardous Substances Data)

Upstream product

• 2216-51-5 (-)-menthol 
• 2905-23-9 2-chlorophenylsulfonyl chloride 
• 95-51-2 o-chloroaniline 
• 45750-59-2 2-chlorobenzenesulphinic acid 

Downstream Products

• 172338-47-5 (R)-(+)-2-chlorophenyl methyl sulfoxide 
• 20268-16-0 (R)-(+)-2-chlorophenyl 4-methylphenyl sulfoxide 

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.

A convenient and highly diastereoselective synthesis of optically active sulfinate esters from sulfonyl chlorides under solid state conditions

A manipulatively simple and rapid method for synthesis of chiral sulfinate esters 1 and 2 from sulfonyl chloride and trimethyl phosphite in solid phase conditions supported on silica gel is described. The chemical yields are good to excellent and diastereoselectivity is high.