139930-06-6

Basic information

• Product Name: Benzene, [(2-bromo-2-propenyl)thio]-
• CAS NO: 139930-06-6
• Molecular Formula: C9H9BrS
• Molecular Weight: 229.14
• Mol File: 139930-06-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzene, [(2-bromo-2-propenyl)thio]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [(2-bromo-2-propenyl)thio]-(139930-06-6)
• EPA Substance Registry System: Benzene, [(2-bromo-2-propenyl)thio]-(139930-06-6)

Safety Data

• Hazardous Substances Data: 139930-06-6(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 513-31-5 2-bromoallyl bromide 
• 930-69-8 sodium thiophenolate 

Downstream Products

• 145732-28-1 2-Bromo-undec-1-ene 
• 53608-85-8 2-bromo-3-cyclohexylprop-1-ene 
• 145732-29-2 3-(3-Bromo-but-3-enyl)-cyclohexanone 
• 1150634-46-0 ethyl 2-phenyl-2-(phenylthio)-4-bromo-4-pentenoate 
• 108-98-5 thiophenol 
• 145732-41-8 1-(2-Bromo-allyl)-3-oxo-cyclohexanecarboxylic acid methyl ester 
• 145732-27-0 1-(2-Bromo-allyl)-1-methyl-cyclohexane 

Relevant articles and documents

Highly chemoselective synthesis of aryl allylic sulfoxides through calcium hypobromite oxidation of aryl allylic sulfides

A highly chemoselective oxidation of widely substituted aryl allylic sulfides, prepared by allylation of arylthioethers with KF-Celite, to the corresponding aryl allylic sulfoxide was achieved by employing calcium hypobromite. Neither over-oxidation to sulfones nor halogenation of the aromatic rings was observed. The protocol may be successfully applied for the oxidation of substituted allylic systems (i.e., 2-haloallyl) that per se could interact with the oxidizing agent.

Cyclizations and Rearrangements of Samarium Diiodide-Generated Vinyl Radicals

Vinyl bromides 1, 5, 15, 20, 23, 27, 33a,b, 41a-c, 44a-c, 46a,b, 52a,b, 55a, 56a,b, and 60a,b react with samarium diiodide in THF and/or acetonitrile to give the corresponding vinyl radicals.Radicals 3, 7, and 16 afforded products deriving from cyclization on the adjacent triple bond in a 5-(?-exo)exo, 6-(?-endo)exo, and 6-(?-exo)exo mode, respectively.Radical 7 undergoes competitive 1,5-hydrogen translocation.Vinyl radicals 21 and 24 readily cyclize on the proximal double bond, leading to 5- and 6-membered rings, respectively.Thienyl-substituted radical 28 leads to a product deriving from 5-exo cyclization on the thiophene ring and subsequent β-fission of the C-S bond, whereas thienyl-substituted radicals 34a,b undergo almost exclusively 1,5-hydrogen translocation.Aryl-substituted radicals obtained from vinyl bromides 41, 44, 46, 52, and 55 do not form any products deriving from 5-exo or 6-exo cyclization (or ipso cyclization).Finally, naphthyl-substituted radicals 57a and 61a give only direct reduction products, whereas the radical 61b affords, in addition to the direct reduction product, a rearranged product deriving from a 1,3-radical migration of the naphthylthio group.Evidence is reported for the reduction of EWG-substituted benzene rings and thio-substituted naphthalene rings to radical anions, which can fragment on the side chain with the elimination of allyl radicals. α-Oxy(and α-thio)-substituted radicals deriving from 1,5-shift rearrange to alcohols (and thiols) through a Wittig rearrangement or a cyclization/fragmentation process.