395-25-5

Basic information

• Product Name: Bis[4-fluorophenyl] sulfoxide
• Synonyms: 1,1'-Sulfinylbis[4-fluorobenzene];Bis(4-fluorophenyl) sulfoxide;Bis[4-fluorophenyl] sulfoxide;4,4'-Difluorodiphenyl sulfoxide;Bis(p-fluorophenyl) sulfoxide;1-fluoro-4-(4-fluorophenyl)sulfinylbenzene
• CAS NO: 395-25-5
• Molecular Formula: C₁₂H₈F₂OS
• Molecular Weight: 238.25
• Mol File: 395-25-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 46.6-47.0℃ (hexane )
• Appearance: /
• CAS DataBase Reference: Bis[4-fluorophenyl] sulfoxide(CAS DataBase Reference)
• NIST Chemistry Reference: Bis[4-fluorophenyl] sulfoxide(395-25-5)
• EPA Substance Registry System: Bis[4-fluorophenyl] sulfoxide(395-25-5)

Safety Data

• Hazardous Substances Data: 395-25-5(Hazardous Substances Data)

Usage

General Description

Bis[4-fluorophenyl] sulfoxide is a chemical compound with the molecular formula (C6H4F)2SO. It is a sulfoxide derivative with two 4-fluorophenyl groups attached to the sulfur atom. Bis[4-fluorophenyl] sulfoxide is commonly used as a reactant in organic synthesis and chemical research. It has been employed in various reactions, including oxidation, asymmetric catalysis, and the synthesis of organofluorine compounds. Additionally, it has potential applications in pharmaceuticals and materials science due to its unique properties and reactivity. Bis[4-fluorophenyl] sulfoxide is a valuable and versatile building block in the synthesis of complex organic molecules and functional materials.

Upstream product

• 7719-09-7 thionyl chloride 
• 462-06-6 fluorobenzene 
• 352-13-6 4-flourophenylmagnesium bromide 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 404-38-6 4,4'-difluorodiphenyl sulfide 
• 108-67-8 1,3,5-trimethyl-benzene 
• 98-08-8 α,α,α-trifluorotoluene 

Downstream Products

• 383-29-9 bis(p-fluorophenyl)sulfone 
• 404-38-6 4,4'-difluorodiphenyl sulfide 
• 167401-85-6 Bis(4-fluorophenyl)-4-tolylsulfonium methanesulfonate 
• 89959-07-9 MoO₂(2,6-bis(2,2-diphenyl-2-mercaptoethyl)pyridine^(2-)) 
• 1294007-16-1 CF₃O₃S^(1-)*C₃₅H₃₀FO₅S₂⁽¹⁺⁾ 
• 1294007-23-0 CF₃O₃S^(1-)*C₃₅H₃₀FO₃S₄⁽¹⁺⁾ 
• 1294007-10-5 CF₃O₃S^(1-)*C₃₂H₂₂F₃O₂S₂⁽¹⁺⁾ 
• 1294007-19-4 CF₃O₃S^(1-)*C₃₂H₂₂F₃O₂S₂⁽¹⁺⁾ 
• 1294007-14-9 CF₃O₃S^(1-)*C₃₁H₂₀F₃OS₂⁽¹⁺⁾ 
• 225916-39-2 2-(4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 324-74-3 4-fluoro-biphenyl 
• 893620-80-9 N-(4-fluorophenyl)pyrimidin-2-ylamine 
• 72358-70-4 N-(4-fluorophenyl)pyridin-2-ylamine 

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.

Desulfurization of Diaryl(heteroaryl) Sulfoxides with Benzyne

Two benzyne-enabled desulfurization reactions have been demonstrated which convert diaryl sulfoxides and heteroaryl sulfoxides to biaryls and desulfurized heteroarenes, respectively. The reaction accessing biaryls tolerates a variety of functional groups, such as halides, pseudohalides, and carbonyls. Mechanistic studies reveal that both reactions proceed via a common assembly process but divergent disassemblies of the generated tetraaryl(heteroaryl) sulfuranes.

Enantioselective Synthesis of Chiral-at-Sulfur 1,2-Benzothiazines by CpxRhIII-Catalyzed C?H Functionalization of Sulfoximines

Sulfoximines with stereogenic sulfur atoms are attractive structural motifs in drug discovery. A direct catalytic enantioselective method for the synthesis of sulfur-chiral 1,2-benzothiazines from readily accessible diaryl sulfoximines is presented. Rhodium(III) complexes equipped with chiral cyclopentadienyl ligands and paired with suitable carboxylic acid additives engage in an enantiodetermining C?H activation directed by the sulfoximine group. Subsequent trapping of the rhodacycle with a broad range of diazoketones gives access to S-chiral 1,2-benzothiazines with synthetically highly attractive substitution patterns in good yields and enantioselectivities.