108789-40-8

Basic information

• Product Name: Benzene, 1-[(phenylsulfinyl)methyl]-4-(trifluoromethyl)-
• CAS NO: 108789-40-8
• Molecular Formula: C14H11F3OS
• Molecular Weight: 284.302
• Mol File: 108789-40-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzene, 1-[(phenylsulfinyl)methyl]-4-(trifluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-[(phenylsulfinyl)methyl]-4-(trifluoromethyl)-(108789-40-8)
• EPA Substance Registry System: Benzene, 1-[(phenylsulfinyl)methyl]-4-(trifluoromethyl)-(108789-40-8)

Safety Data

• Hazardous Substances Data: 108789-40-8(Hazardous Substances Data)

Upstream product

• 28715-70-0 methoxy-phenyl-sulfane 
• 402-49-3 4-bromomethyltrifluoromethylbenzene 
• 30932-37-7 phenyl(4-(trifluoromethyl)benzyl)sulfane 
• 31268-20-9 bromomethyl phenyl sulfoxide 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 201230-82-2 carbon monoxide 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 108-98-5 thiophenol 
• 6952-59-6 3-cyanobromobenzene 
• 623-00-7 4-bromobenzenecarbonitrile 

Relevant articles and documents

Competitive and selective Csp3-Br versus Csp2-Br bond activation in palladium-catalysed Suzuki cross-coupling: An experimental and theoretical study of the role of phosphine ligands

Phosphine ligands have been demonstrated to have an effect on reactivity and selectivity in the competitive intramolecular palladium-catalysed Suzuki-Miyaura coupling of dibromo sulfoxide 1a possessing two different hybridised electrophilic carbons. It was found that the bromine bond to the sp3-hybridised carbon is selectively replaced in the presence of unhindered phosphines such as PPh3 or xantphos. The use of hindered phosphine ligands such as P(o-tol)3 and P(1-naphthyl)3 reversed the selectivity, conducting the cross-coupling at the Csp 2-Br. Identical trends were observed in external competition experiments carried out with bromomethyl sulfoxide and different substituted bromoarenes. DFT and DFT/MM calculations showed that the selectivity observed is mainly due to the different facility of the ligands to dissociate. Bisphosphine catalysts favour coupling at the sp3 carbon, whereas monophosphine catalysts prefer the sp2 carbon. Customised catalysts: Proper selection of the phosphine ligand in the palladium catalyst enables a highly intra- and intermolecular selective Suzuki-Miyaura coupling at either Csp 3-Br or Csp2-Br (see figure). DFT and DFT/MM calculations show that the selectivity observed is mainly due to the different facilities of the ligands for dissociation. Copyright

Palladium-catalyzed reaction of boronic acids with chiral and racemic α-bromo sulfoxides

Palladium-catalyzed cross-coupling reactions of racemic α-bromo sulfoxides with boronic acids are carried out in either aqueous or nonaqueous medium with formation of a new C sp3-C sp2 bond. The arylation of chiral α-bromo sulfoxides occurs without racemization. The cross-coupling reaction is general and gives high yields with arylboronic acids substituted with either donor or acceptor groups but gives poor results with heteroarylboronic acids. The best yields are obtained using degassed solvents and CsF instead of aqueous base. The use of aqueous base and the presence of oxygen favor the homocoupling side reaction.

THE THIO-ARBUZOV-REACTION. PART 7. UNSYMMETRIC SULFOXIDES PhS(O)CH2R FROM METHYL BENZENESULFENATE AND BROMOALKANES RCH2Br

Alkylation reactions of methyl benzenesulfenate with bromoalkanes were studied and found to follow the Thio-ARBUZOV pathway.The reaction concept was extended to the conversion of sulfenates into unsymmetric sulfoxides.Thus four new unsymmetric sulfoxides could be obtained and the synthesis of others already mentioned in the literature was improved. Key words: Thio-ARBUZOV-Reaction; methyl benzenesulfenate; bromoalkanes; unsymmetric sulfoxides; nitromethane; 19F-NMR data.