398126-90-4

Basic information

• Product Name: Benzene, 1-[(4-methoxyphenyl)sulfinyl]-4-(trifluoromethyl)-
• CAS NO: 398126-90-4
• Molecular Formula: C14H11F3O2S
• Molecular Weight: 300.301
• Mol File: 398126-90-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzene, 1-[(4-methoxyphenyl)sulfinyl]-4-(trifluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-[(4-methoxyphenyl)sulfinyl]-4-(trifluoromethyl)-(398126-90-4)
• EPA Substance Registry System: Benzene, 1-[(4-methoxyphenyl)sulfinyl]-4-(trifluoromethyl)-(398126-90-4)

Safety Data

• Hazardous Substances Data: 398126-90-4(Hazardous Substances Data)

Upstream product

• 696-63-9 4-Methoxybenzenethiol 
• 455-13-0 4-Iodobenzotrifluoride 
• 825-83-2 4-trifluoromethylbenzenethiol 
• 31401-23-7 p-methoxybenzenesulfinyl chloride 
• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 
• 53451-91-5 1-[(4-methoxyphenyl)thio]-4-(trifluoromethyl)benzene 
• 402-54-0 p-nitrobenzotrifluoride 

Downstream Products

• 1158986-98-1 4'-chloro-2-((4-methoxyphenyl)sulfinyl)-5-(trifluoromethyl)-1,1'-biphenyl 
• 214360-65-3 4-trifluoromethylphenylboronic acid pinacol ester 
• 18158-44-6 4-dimethylamino-4'-methoxybiphenyl 
• 117530-20-8 N,N-dimethyl-4′-(trifluoromethyl)-[1,1′-biphenyl]-4-amine 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 501374-30-7 5,5-dimethyl-2-(4-trifluoromethyl-phenyl)-[1,3,2]dioxaborinane 

Relevant articles and documents

Ni-Catalyzed Borylation of Aryl Sulfoxides

A nickel/N-heterocyclic carbene (NHC) catalytic system has been developed for the borylation of aryl sulfoxides with B2(neop)2 (neop=neopentyl glycolato). A wide range of aryl sulfoxides with different electronic and steric properties were converted into the corresponding arylboronic esters in good yields. The regioselective borylation of unsymmetric diaryl sulfoxides was also feasible leading to borylation of the sterically less encumbered aryl substituent. Competition experiments demonstrated that an electron-deficient aryl moiety reacts preferentially. The origin of the selectivity in the Ni-catalyzed borylation of electronically biased unsymmetrical diaryl sulfoxide lies in the oxidative addition step of the catalytic cycle, as oxidative addition of methoxyphenyl 4-(trifluoromethyl)phenyl sulfoxide to the Ni(0) complex occurs selectively to give the structurally characterized complex trans-[Ni(ICy)2(4-CF3-C6H4){(SO)-4-MeO-C6H4}] 4. For complex 5, the isomer trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I was structurally characterized in which the phenyl sulfinyl ligand is bound via the oxygen atom to nickel. In solution, the complex trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I is in equilibrium with the S-bonded isomer trans-[Ni(ICy)2(C6H5)(SOC6H5)] 5, as shown by NMR spectroscopy. DFT calculations reveal that these isomers are separated by a mere 0.3 kJ/mol (M06/def2-TZVP-level of theory) and connected via a transition state trans-[Ni(ICy)2(C6H5)(η2-{SO}-C6H5)], which lies only 10.8 kcal/mol above 5.

Palladium-Catalyzed Double Borylation of Diaryl Sulfoxides with Diboron

Borylation of the C-S bond of diaryl sulfoxides with bis(pinacolato)diboron (B 2 pin 2) is accomplished by means of a phosphine-ligated palladium catalyst and LiN(SiMe 3) 2 as a base. Both of the aryl rings of the diaryl sulfoxides are converted into borylated products.

Meta- and para-difunctionalization of arenes via an ortho-magnesiation and a subsequent sulfoxide-magnesium exchange

Highly functionalized 1,2,4-trisubstituted arenes can be prepared on large scale by a two-step sequence, triggered by an aryl sulfoxide group. In the first step, the sulfoxide moiety acts as a metalation directing group, allowing a smooth magnesiation wit