171617-77-9

Basic information

• Product Name: (Ss)-3-bromo-2-(p-tolylsulfinyl)-furane
• Synonyms: (Ss)-3-bromo-2-(p-tolylsulfinyl)-furane
• CAS NO: 171617-77-9
• Molecular Weight: 285.161
• Mol File: 171617-77-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (Ss)-3-bromo-2-(p-tolylsulfinyl)-furane(CAS DataBase Reference)
• NIST Chemistry Reference: (Ss)-3-bromo-2-(p-tolylsulfinyl)-furane(171617-77-9)
• EPA Substance Registry System: (Ss)-3-bromo-2-(p-tolylsulfinyl)-furane(171617-77-9)

Safety Data

• Hazardous Substances Data: 171617-77-9(Hazardous Substances Data)

Upstream product

• 30544-34-4 2,3-dibromofuran 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 22037-28-1 3-bromofurane 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 

Downstream Products

• 159169-40-1 2-(Toluene-4-sulfinyl)-furan 
• 177849-46-6 3-(p-tolylsulfinyl)-2-furaldehyde 

Relevant articles and documents

Synthesis of C3-substituted enantiopure 2-(p-tolylsulfinyl)-furans: The sulfoxide group as a chiral inductor for furan dienes as precursors of a wide variety of chiral intermediates

(-)-(1R,2S,5R)-Menthyl (SS)-p-toluenesulfinate and its enantiomer are a common source for a chiral sulfoxide group in organic synthesis, by means of nucleophilic substitution. The replacement of the menthyloxy group, with complete inversion of configuration at the sulfur center of the chiral sulfoxide, allows the inclusion of this organic function into numerous substrates, with defined stereochemistry and high enantiomeric purity. Nine C3-substituted, enantiomerically pure, 2-sulfinylfurans were prepared by this synthetic methodology with moderate to high yields. These enantiopure C3-substituted 2-sulfinylfurans can be used as chiral dienes for [4+3] cycloaddition reactions and in other chemical transformations, in which π-facial selectivity should be induced in order to obtain enantioselective reactions.