3459-94-7

Usage

Uses

Used in Chemical Synthesis:
Benzene, 1,4-bis(phenylthio)is used as a building block in the synthesis of various polymers and organic compounds, contributing to the development of new materials with specific properties for different applications.
Used in Rubber and Plastics Production:
As a cross-linking agent, Benzene, 1,4-bis(phenylthio)enhances the strength and durability of rubbers and plastics, improving their performance in various industrial and consumer products.
Used in Photoconductor Materials:
Benzene, 1,4-bis(phenylthio)has been studied for its potential use in photoconductor materials, which are crucial in the functioning of devices such as photocopiers and laser printers.
Used in Organic Electronic Devices:
Benzene, 1,4-bis(phenylthio)is also considered as a component in the development of organic electronic devices, which are known for their flexibility and potential for lower-cost manufacturing processes.

Upstream product

• 106-46-7 para-dichlorobenzene 
• 1192-40-1 copper(I) thiophenolate 
• 52599-10-7 (4-bromo-phenyl)-phenylsulfanyl-diazene 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 930-69-8 sodium thiophenolate 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 108-98-5 thiophenol 
• 106-37-6 1.4-dibromobenzene 
• 106-39-8 bromochlorobenzene 
• 98-80-6 phenylboronic acid 
• 637-87-6 1-Chloro-4-iodobenzene 
• 4612-26-4 1,4-Phenyldiboronic acid 
• 873-55-2 sodium benzenesulfonate 

Downstream Products

• 27375-45-7 1,4-bis-benzenesulfonyl-benzene 
• 241-34-9 benzo[1, 2-b: 4, 5-b']bis[b]benzothiophene 
• 59090-58-3 1-(phenylsulfinyl)-4-(phenylsulfinyl)benzene 
• 134983-66-7 C₃₀H₂₂O₈S₄ 
• 134983-65-6 1,4-bis((4-bromophenyl)sulfonyl)benzene 
• 3379-65-5 1,4-di(p-phenylthio)phenylthiobenzene 
• 99901-62-9 C₁₈H₁₄S₂O 
• 41518-53-0 1,4-bis((4-bromophenyl)thio)benzene 
• 71449-78-0 4-thiophenoxyphenyl(diphenyl)sulfonium hexafluoroantimonate 

Relevant academic research and scientific papers

Environmentally Friendly and Recyclable CuCl 2-Mediated C-S Bond Coupling Strategy Using DMEDA as Ligand, Base, and Solvent

Simple reaction conditions and recyclable reagents are crucial for environmentally friendly industrial applications. An environment-friendly, recyclable and economic strategy was developed to synthesize diaryl chalcogenides by the CuCl2-catalyzed C S bondformation reaction via iodobenzenes and benzenethiols/1,2-diphenyldisulfanes using N,N'-dimethylethane-1,2-diamine (DMEDA) as ligand, base, and solvent. For these reactions, especially the reactions of diiodobenzenes and aminobenzenethiols/disulfanediyldianilines, a range of substrates are compatible and give the corresponding products in good to excellent yields. Both of the reagents in the catalytic system (CuCl2/DMEDA) are inexpensive, conveniently separable, and recyclable for more than five cycles.

Dimsyl Anion Enables Visible-Light-Promoted Charge Transfer in Cross-Coupling Reactions of Aryl Halides

A methodology is reported for visible-light-promoted synthesis of unsymmetrical chalcogenides enabled by dimsyl anion in the absence of transition-metals or photoredox catalysts. The cross-coupling reaction between aryl halides and diaryl dichalcogenides proceeds with electron-rich, electron-poor, and heteroaromatic moieties. Mechanistic investigations using UV-Vis spectroscopy, time-dependent density functional theory (TD-DFT) calculations, and control reactions suggest that dimsyl anion forms an electron-donor-acceptor (EDA) complex capable of absorbing blue light, leading to a charge transfer responsible for generation of aryl radicals from aryl halides. This previously unreported mechanistic pathway may be applied to other light-induced transformations performed in DMSO in the presence of bases and aryl halides.

Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C?S/C?N Couplings

Ni-catalyzed C?S cross-coupling reactions have received less attention compared with other C-heteroatom couplings. Most reported examples comprise the thioetherification of most reactive aryl iodides with aromatic thiols. The use of C?O electrophiles in this context is almost uncharted. Here, we describe that preformed Ni(II) precatalysts of the type NiCl(allyl)(PMe2Ar’) (Ar’=terphenyl group) efficiently couple a wide range of (hetero)aryl halides, including challenging aryl chlorides, with a variety of aromatic and aliphatic thiols. Aryl and alkenyl tosylates are also well tolerated, demonstrating, for the first time, to be competent electrophilic partners in Ni-catalyzed C?S bond formation. The chemoselective functionalization of the C?I bond in the presence of a C?Cl bond allows for designing site-selective tandem C?S/C?N couplings. The formation of the two C-heteroatom bonds takes place in a single operation and represents a rare example of dual electrophile/nucleophile chemoselective process.

Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds

A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.

A Visible-Light-Harvesting Covalent Organic Framework Bearing Single Nickel Sites as a Highly Efficient Sulfur–Carbon Cross-Coupling Dual Catalyst

Covalent Organic Frameworks (COFs) have recently emerged as light-harvesting devices, as well as elegant heterogeneous catalysts. The combination of these two properties into a dual catalyst has not yet been explored. We report a new photosensitive triazine-based COF, decorated with single Ni sites to form a dual catalyst. This crystalline and highly porous catalyst shows excellent catalytic performance in the visible-light-driven catalytic sulfur–carbon cross-coupling reaction. Incorporation of single transition metal sites in a photosensitive COF scaffold with two-component synergistic catalyst in organic transformation is demonstrated for the first time.

Generation of Aryl Radicals from Aryl Halides: Rongalite-Promoted Transition-Metal-Free Arylation

A new and practical method for the generation of aryl radicals from aryl halides is reported. Rongalite as a novel precursor of super electron donors was used to initiate a series of electron-catalyzed reactions under mild conditions. These transition-metal-free radical chain reactions enable the efficient formation of C-C, C-S, and C-P bonds through homolytic aromatic substitution or SRN1 reactions. Moreover, the synthesis of antipsychotic drug Quetiapine was performed on gram scale through the described method. This protocol demonstrated its potential as a promising arylation method in organic synthesis.

A semiconducting supramolecular Co(ii)-metallohydrogel: an efficient catalyst for single-pot aryl-S bond formation at room temperature

A novel mechanically stable supramolecular Co(ii)-metallohydrogel has been synthesized. Cobalt(ii) nitrate hexahydrate and monoethanolamine, as a low molecular weight organic gelator, are used to get the gel. The mechanical stability of the supramolecular hydrogel was analyzed. The morphology of the supramolecular metallohydrogel was scrutinized. The semiconducting features of the metallohydrogel were studied. The conducting properties of the Co(ii)-metallohydrogel establish a Schottky barrier diode type nature. The catalytic nature of the Co(ii)-metallohydrogel based room temperature single pot aryl-S coupling reaction was explored. Most interestingly, the Co(ii)-metallohydrogel based catalytic aryl-S coupling reaction does not require any column-chromatographic purification protocol to get pure aryl-thioethers. Thus, through this work a semiconducting Schottky barrier diode application and catalytic role in the room temperature single pot aryl-S coupling reaction of a supramolecular Co(ii)-metallohydrogel have been explored.

CuFe2O4 magnetic nanoparticle catalyzed odorless synthesis of sulfides using phenylboronic acid and aryl halides in the presence of S8

CuFe2O4 magnetic nanoparticles were prepared, characterized and used as a magnetically recoverable nanocatalyst for the one-pot synthesis of phenyl aryl/heteroaryl/benzyl sulfides through the cross-coupling reaction of phenylboronic acid with aryl/heteroaryl/benzyl halides in the presence of S8 as a sulfur source in PEG400 as a reusable solvent at 80 °C. Also, the synthesis of symmetrical sulfides from aryl/heteroaryl halides using S8, KF and Cs2CO3 in PEG400 at 120 °C is described. The magnetic nanocatalyst was recycled up to 6 times with little loss of activity.

Disulfides as efficient thiolating reagents enabling selective bis-sulfenylation of aryl dihalides under mild copper-catalyzed conditions

Selective bis-sulfenylation reactions of aryl dihalides have been achieved by copper-catalyzed C-S coupling reactions under mild conditions of refluxing EtOH (80 °C). Employment of disulfides as thiolating reagents enables the production of various bis(phenylthio)benzenes with excellent selectivity, and no products from mono C-S coupling are isolated. the Partner Organisations 2014.

Synthesis of dibenzothiophenes by pd-catalyzed dual C-H activation from diaryl sulfides

Palladium-catalyzed dual C-H functionalization of diaryl sulfides to form dibenzothiophenes (DBTs) by oxidative dehydrogenative cyclization is reported. This protocol afforded various DBTs in moderate to good yields with tolerance of a wide variety of substrates. Benzo[1,2-b:4,5-b]bis[b]benzothiophene was successfully synthesized by this method, which was used as an organic semiconductor for field-effect transistors.