5633-55-6

Usage

Uses

Used in Pharmaceutical Industry:
4-Phenylthiophenol is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its ability to facilitate the creation of diverse organic molecules. Its antioxidant and antibacterial properties also contribute to its potential use in developing new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Phenylthiophenol serves as a precursor for the development of new agrochemicals, leveraging its chemical reactivity to produce compounds with pesticidal or herbicidal properties.
Used in Materials Science:
4-Phenylthiophenol is utilized as a building block in the synthesis of advanced materials, taking advantage of its chemical properties to engineer materials with specific characteristics for various applications.
Used in Industrial Applications:
4-Phenylthiophenol's strong antioxidant properties make it suitable for use in industrial applications where protection against oxidation is necessary, such as in the manufacturing of plastics and other synthetic materials.
Used in Medical Applications:
4-PHENYLTHIOPHENOL's antibacterial properties suggest potential uses in medical applications, possibly in the development of new antibiotics or as a component in disinfectants and sanitizers.

Upstream product

• 5633-57-8 1-methoxy-4-(phenylsulfanyl)benzene 
• 618-41-7 Benzenesulfinic acid 
• 108-95-2 phenol 
• 60-29-7 diethyl ether 
• 931-59-9 benzenesulfenyl chloride 
• 108-98-5 thiophenol 
• 106-48-9 4-chloro-phenol 
• 10035-10-6 hydrogen bromide 
• 108-24-7 acetic anhydride 
• 108-86-1 bromobenzene 
• 637-89-8 4-sulfanylphenol 
• 540-38-5 p-Iodophenol 
• 15015-57-3 bis(4-hydroxyphenyl)disulfide 
• 98-80-6 phenylboronic acid 

Downstream Products

• 14763-63-4 4-benzenesulfinyl-phenol 
• 111501-42-9 (2-dimethylcarbamoyloxy-5-phenylsulfanyl-benzyl)-trimethyl-ammonium; bromide 
• 445283-57-8 4-phenylsulfanylphenoxyethyl tetrahydro-2H-pyran-2-yl ether 
• 65962-17-6 4-(phenylthio)phenoxyethanol 
• 60677-93-2 propargyloxy-[4-(phenylmercapto)-phenoxy]-methane 
• 931-59-9 benzenesulfenyl chloride 
• 882-33-7 diphenyldisulfane 
• 3112-84-3 4-methoxyphenyl phenyl sulfone 
• 7402-69-9 p-hydroxyphenyl p-tolyl sulfone 
• 445283-60-3 4-phenylsulfinylphenoxyethyl 4-toluenesulfonate 
• 445283-58-9 2-[2-(4-benzenesulfinyl-phenoxy)-ethoxy]-tetrahydro-pyran 
• 445283-59-0 4-phenylsulfinylphenoxyethanol 
• 5633-57-8 1-methoxy-4-(phenylsulfanyl)benzene 

Relevant academic research and scientific papers

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.

N-bromosuccinimide/HCl mediated reduction of sulfoxides to sulfides

An efficient reduction of sulfoxides to sulfides mediated by N-bromosuccinimide (NBS)/HCl system has been developed. This protocol shows good functional group compatibility as well as broad substrates scope with operational simplicity.

Microwave-Assisted Copper Slag-Catalyzed Green S-Arylation of Arenethiols with Arylboronic Acids

Abstract: Diaryl sulfides have been synthesized in moderate to excellent yield by S-arylation of arenethiols with arylboronic acids using copper slag as a catalyst. Copper slag is a by-product obtained from smelting and refining of copper. Conventional heating method has been compared with the microwave-assisted technique. The proposed microwave-assisted synthesis provides excellent yields of diaryl sulfides in a short time (10 min) and is ligand-free, green, and cost-effective.

Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: Synthesis of diarylsulfides

A NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air. This methodology is reliable and offers a mild and easy to operate process for the synthesis of arylthioethers, which are essential compounds with applications in the pharmaceutical and agricultural industries. This method avoids the use of expensive transition metals, such as Pd, Ir or Rh, sophisticated ligands and elevated temperatures. It also has a wide substrate scope (55 examples) and provides products in good to excellent yields (72-93%).

Achieving Nickel Catalyzed C-S Cross-Coupling under Mild Conditions Using Metal-Ligand Cooperativity

A simple and efficient approach of C-S cross-coupling of a wide variety of (hetero)aryl thiols and (hetero)aryl halides under mild conditions, mostly at room temperature, catalyzed by well-defined singlet diradical Ni(II) catalysts bearing redox noninnocent ligands is reported. Taking advantage of ligand centered redox events, the high-energetic Ni(0)/Ni(II) or Ni(I)/Ni(III) redox steps were avoided in the catalytic cycle. The cooperative participation of both nickel and the coordinated ligands during oxidative addition/reductive elimination steps allowed us to perform the catalytic reactions under mild conditions.

CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides

In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.

Phenyldithiocarbamates: Efficient Sulfuration Reagents in the Chan–Lam Coupling Reaction

The Chan–Lam coupling reaction starting from phenyldithiocarbamates and phenylboronic acids is reported. To avoid using the volatile, hazardous, and foul-smelling thiols, which are sometimes expensive and not sufficiently available, phenyldithiocarbamates can be employed. They are demonstrated to be good sulfuration reagents in the Chan–Lam coupling to prepare biaryl sulfides. By using this protocol, dithiocarbamate substrates with a wide range of functional groups including electron-rich and electron-deficient ones are explored to obtain the desired substituted biaryl sulfides smoothly. This method is ligand-free, has a broad substrate scope, enables good yields, and is easy to perform. It provides a facile and convenient preparation of biaryl sulfides.

PHOTOCATALYST-FREE, LIGHT-INDUCED CARBON-SULFUR CROSS-COUPLING METHODS

In one aspect, the invention provides a method of promoting a carbon-sulfur bond forming reaction. In certain embodiments, the reaction comprises cross-coupling of a(n) (hetero)aryl halide with a thiol to form the carbon-sulfur bond, wherein the method is promoted by light irradiation in the absence of a photocatalyst. In other embodiments, the cross-coupling reaction can be promoted through visible light irradiation, including sunlight.

Nickel-Catalyzed C–S Coupling: Synthesis of Diaryl Sulfides Starting from Phenyldithiocarbamates and Iodobenzenes

A nickel-catalyzed C–S bond-formation protocol for the synthesis of diaryl sulfides is described. In a reaction catalyzed by NiCl2, phenyldithiocarbamates react with iodobenzenes to give diaryl sulfides smoothly in good to excellent yields (66–93 %). The catalyst is cheap, the reaction is easy to carry out, the substrate scope is broad, and the yields are good. Thus, this gives an alternative way to prepare diaryl sulfides.

Visible-light-promoted C-S cross-coupling via intermolecular charge transfer

Disclosed is a mild, scalable, visible-lightpromoted cross-coupling reaction between thiols and aryl halides for the construction of C-S bonds in the absence of both transition metal and photoredox catalysts. The scope of aryl halides and thiol partners includes over 60 examples and therefore provides an entry point into various aryl thioether building blocks of pharmaceutical interest. Furthermore, to demonstrate its utility, this C-S coupling protocol was applied in drug synthesis and latestage modifications of active pharmaceutical ingredients. UV-vis spectroscopy and time-dependent density functional theory calculations suggest that visible-lightpromoted intermolecular charge transfer within the thiolate-aryl halide electron donor-acceptor complex permits the reactivity in the absence of catalyst.