1191465-70-9

Basic information

• Product Name: (R(S))-(-)-1-(tert-butylsulfinyl)-3-methoxybenzene
• Synonyms: (R(S))-(-)-1-(tert-butylsulfinyl)-3-methoxybenzene
• CAS NO: 1191465-70-9
• Molecular Weight: 212.313
• Mol File: 1191465-70-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R(S))-(-)-1-(tert-butylsulfinyl)-3-methoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: (R(S))-(-)-1-(tert-butylsulfinyl)-3-methoxybenzene(1191465-70-9)
• EPA Substance Registry System: (R(S))-(-)-1-(tert-butylsulfinyl)-3-methoxybenzene(1191465-70-9)

Safety Data

• Hazardous Substances Data: 1191465-70-9(Hazardous Substances Data)

Upstream product

• 2398-37-0 3-methoxyphenyl bromide 
• 67734-35-4 (R)-tert-butyl tert-butanethiosulfinate 
• 159263-57-7 (R)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl tert-butanesulfinate 
• 636607-99-3 C₁₂H₉BO₃S 

Downstream Products

• 1310329-88-4 (R)-benzyl (2-(tert-butylsulfinyl)-6-methoxyphenyl) sulfane 
• 1241905-88-3 (R)-(2-(tert-butylsulfinyl)-6-methoxyphenyl)diphenylphosphine 
• 1191465-97-0 (S)-ethyl 2-(3-methoxyphenylsulfinyl)acetate 

Relevant articles and documents

DMAP-Catalysed Sulfinylation of Diacetone- D -Glucose: Improved Method for the Synthesis of Enantiopure tert-Butyl Sulfoxides and tert-Butanesulfinamides

An improved method for the tert-butanesulfinylation of diacetone glucose with tert-butanesulfinyl chloride is reported. The method is based on a beneficial effect of catalytic DMAP, which enhances both the rate of the reaction and the enantioselectivity of the process to give (R S)-diastereomer 2 R S with a 94 % de and in quantitative yield. (R S)-DAG sulfinate ester 2 R S is an excellent intermediate for the synthesis of enantiopure tert-butyl sulfoxides. Grignard agents and organolithium reagents can displace smoothly the diacetone glucose moiety to give synthetically relevant enantiopure sulfoxides, including highly functionalized derivatives, in high yields and with high enantioselectivities. (R S)-DAG sulfinate ester 2 R S is also an excellent N-sulfinylating agent; simple addition of LiHMDS (lithium hexamethyldisilazide) in THF gives (S S)-tert-butanesulfinamide, and N-tert-butanesulfinylimines are then formed in a two-step one-pot manner. N-Alkylated tert-butanesulfinamides are formed by the condensation of 2 R S with lithium amides.

Axial chirality control during suzuki-miyaura cross-coupling reactions: The tert-Butylsulfinyl group as an efficient chiral auxiliary

An efficient route to a new family of axially chiral biaryl ligands by a Suzuki-Miyaura cross-coupling reaction between ortho,ortho'-disubstituted aryl iodides bearing in ortho position a tert-butyl or p-tolylsulfinyl group and ortho-substituted phenyl boronic acids or esters is described. The comparison between the t-BuSO and p-TolSO groups as chiral controllers is reported. The modularity of the approach is demonstrated by the preparation of a variety of enantiopure axially chiral mixed S/N and S/P ligands.