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

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

Uses

Used in Organic Synthesis:
Bis[4-fluorophenyl] sulfoxide is used as a reactant in organic synthesis for its ability to participate in various chemical reactions, such as oxidation, asymmetric catalysis, and the synthesis of organofluorine compounds. Its reactivity and unique properties make it a valuable component in creating complex organic molecules.
Used in Chemical Research:
In the field of chemical research, Bis[4-fluorophenyl] sulfoxide is utilized as a reactant to explore new reaction pathways and mechanisms, contributing to the advancement of chemical knowledge and the development of novel synthetic methods.
Used in Pharmaceutical Industry:
Bis[4-fluorophenyl] sulfoxide is used as a building block in the pharmaceutical industry for its potential applications in the development of new drugs. Its unique structure and reactivity can be harnessed to create molecules with specific biological activities, contributing to the discovery of innovative therapeutic agents.
Used in Materials Science:
In materials science, Bis[4-fluorophenyl] sulfoxide is employed as a component in the synthesis of functional materials. Its incorporation into material structures can impart desired properties, such as improved stability, enhanced performance, or specific interactions with other molecules, making it a valuable asset in the development of advanced materials for various applications.

Upstream product

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

Downstream Products

• 89959-07-9 MoO₂(2,6-bis(2,2-diphenyl-2-mercaptoethyl)pyridine^(2-)) 
• 404-38-6 4,4'-difluorodiphenyl sulfide 
• 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⁺⁾ 
• 398-23-2 4,4'-difluorobiphenyl 
• 383-29-9 bis(p-fluorophenyl)sulfone 
• 225916-39-2 2-(4-fluorophenyl)-5,5-dimethyl-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.

Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides

A highly chemoselective, efficient and nano-Pd catalyzed protocol for the rapid construction of sulfoxides and sulfones via the oxidation of symmetrical and unsymmetrical sulfides using H2O2 as an oxidant has been developed, respectively. The ready availability of starting materials, easy recovery and reutilization of the catalyst, wide substrate scope, and high yields make this protocol an attractive alternative. The process also involves the metal-free and microwave-promoted synthesis of symmetrical diarylsulfides, and FeCl3-mediated preparation of symmetrical diaryldisulfides through the reaction of arenediazonium tetrafluoroborates with Na2S·9H2O as a sulfur source. In addition, unsymmetrical sulfides were generated via the K2CO3-mediated reaction of arenediazonium tetrafluoroborates with symmetrical disulfides.

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.

Redox-Neutral Synthesis of Selenoesters by Oxyarylation of Selenoalkynes under Mild Conditions

An approach for the mild synthesis of selenoesters starting from selenoalkynes through an acid-catalyzed, redox-neutral oxyarylation reaction is reported. Br?nsted acid activation of a selenoalkyne leads to a selenium-stabilized vinyl cation, which is cap

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.

Selective oxidation of sulfides to sulfoxides with cyanuric chloride and urea-hydrogen peroxide adduct

Although a number of methods have been developed for the selective oxidation of sulfides to sulfoxides, the need remains for alternative efficient, reliable strategies that can be generally applied to various sulfides and that use readily available reagents under mild reaction conditions. Herein, we report the use of urea-hydrogen peroxide adduct (UHP) and cyanuric chloride in CH 3CN at room temperature to convert sulfides to sulfoxides in excellent yields. In particular, this protocol produced sulfoxides with aromatic rings bearing electron-withdrawing groups in excellent yields.

No-carrier-added [18F]fluoroarenes from the radiofluorination of diaryl sulfoxides

No-carrier-added [18F]fluoroarenes were synthesized through the radiofluorination of diaryl sulfoxides with [18F]fluoride ion. Diaryl sulfoxides bearing a para electron-withdrawing substituent readily gave the corresponding 4-[18F]fluoroarenes in high RCYs. This process broadens the scope for preparing novel 18F-labeling synthons and PET radiotracers.

Polystyrene and silica gel-supported, AlCl3-catalyzed preparation of diaryl sulfoxides from arenes and thionyl chloride

A simple, chemoselective, and efficient method has been developed for direct conversion of arenes to symmetrical diaryl sulfoxides using thionyl chloride in the presence of a catalytic amount of cross-linked polystyrene-supported aluminium chloride (Ps-AlCl3) and silica gel-supported aluminium chloride (SiO2-AlCl3). These solid acid catalysts are stable and can be easily recovered and reused without appreciable change in their efficiency. Copyright Taylor & Francis Group, LLC.

Lithium/Sodium Perchlorate Catalyzed Synthesis of Symmetrical Diaryl Sulfoxides

Synthesis of diaryl sulfoxides from aromatics and thionyl chloride catalyzed by LiClO4/NaClO4 at room temperature is described. Mild reaction conditions, simple work-up, inexpensive and easily available catalysts are important and attractive features of this method.