2974-10-9

Usage

Appearance

White to pale yellow solid

Solubility

Insoluble in water, soluble in organic solvents

Uses

Building block in the synthesis of various organic compounds and materials
Production of polymers and liquid crystals
Crosslinking agent in polymers for electronic devices
Stabilizer in the manufacturing of plastics

Applications

Potential use in organic electronics and optoelectronic devices due to unique molecular structure and electronic properties

Hazard

Considered hazardous if not properly managed

InChI:InChI=1/C18H14S2/c1-3-8-15(9-4-1)19-17-12-7-13-18(14-17)20-16-10-5-2-6-11-16/h1-14H

Upstream product

• 13133-62-5 thiophenolate 
• 625-99-0 3-iodochlorobenzene 
• 456-39-3 3-chlorobenzenediazonium tetrafluoroborate 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 541-73-1 1,3-Dichlorobenzene 
• 108-36-1 1,3-dibromobenzene 
• 882-33-7 diphenyldisulfane 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 626-00-6 1,3-Diiodobenzene 
• 873-55-2 sodium benzenesulfonate 
• 4612-28-6 1,3-phenylenediboronic acid 
• 591-18-4 1-Bromo-3-iodobenzene 
• 114650-60-1 C₁₂H₉BrN₂S 

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.

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.

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.

Room-Temperature Arylation of Thiols: Breakthrough with Aryl Chlorides

The formation of aryl C?S bonds is an important chemical transformation because aryl sulfides are valuable building blocks for the synthesis of biologically and pharmaceutically active molecules and organic materials. Aryl sulfides have traditionally been synthesized through the transition-metal-catalyzed cross-coupling of aryl halides with thiols. However, the aryl halides used are usually bromides and iodides; readily available, low-cost aryl chlorides often not reactive enough. Furthermore, the deactivation of transition-metal catalysts by thiols has forced chemists to use high catalyst loadings, specially designed ligands, high temperatures, and/or strong bases, thus leading to high costs and the incompatibility of some functional groups. Herein, we describe a simple and efficient visible-light photoredox arylation of thiols with aryl halides at room temperature. More importantly, various aryl chlorides are also effective arylation reagents under the present conditions.

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.

Ligand-free highly effective iron/copper co-catalyzed formation of dimeric aryl ethers or sulfides

Highly selective coupling of diiodoarenes with phenols or phenthiols can be performed by using a low-cost, benign character and readily available Fe/Cu catalytic system in the absence of ligands. It is noteworthy that the desired dimeric aryl ethers or sulfides could be obtained in high yields by coupling between diiodoarenes and phenols, or diphenols with aryl iodides. The Royal Society of Chemistry 2011.

Efficient copper-catalyzed S-arylation of thiols with aryl bromides and chlorides

An efficient copper-catalyzed system for C-S cross-coupling of aromatic thiols with aryl bromides and chlorides has been developed using 1,2,3,4-tetrahydroquinoline-8-ol as a ligand. It is noteworthy that this method is proved to be especially effective for aryl bromides with electron-donating groups. By this protocol, a variety of thioethers as well as symmetrical and unsymmetrical bis-thioethers are obtained in excellent yields with an exceptional level of functional group tolerance and high chemoselectivity. Georg Thieme Verlag Stuttgart - New York.

Ligand-free copper-catalyzed C-S coupling of aryl iodides and thiols

(Chemical Equation Presented) A protocol for the copper-catalyzed aryl-sulfur bond formation between aryl iodides and thiophenols is reported. The reaction is catalyzed by a low amount (1-2.5 mol %) of readily available and ligand-free copper iodide salt. A variety of diaryl thioethers are synthesized under relatively mild reaction conditions with good chemoselectivity and functional group tolerance.

HEAT-RESISTANT LUBRICATING OIL COMPOSITION

There are provided a heat resistant lubricating oil composition comprising a lubricating base oil comprising an organic ester or a mixture of an organic ester and a polyphenyl ether or an organopolysiloxane, and incorporated with from 0.05% by weight to 1

INNOVATIVE APPROACH TO THE SYNTHESIS OF SULPHIDES AND THEIR CORRESPONDING SULPHONES

A general and efficient synthetic approach to aryl-aryl bis-sulphides with aliphatic or aromatic bridges via the nucleophilic aromatic substitution (SNAr) of cyclopentadienyliron arene complexes with a number of dithiols followed by photolytic demetallation is presented in this work.The oxidation of the bis(cyclopentadienyliron) arene complexes containing bis-sulphide linkages with 3-chlorobenzoic acid gave their corresponding sulphones in very good yield (70-95percent).Mixed ether/sulphide and ether/sulphone complexes were also prepared following the same synthetic strategy.Reactions of sulphide and sulphone diiron complexes with terminal chloro groups with a number of oxygen, sulphur and carbon nucleophiles allowed for the functionalization of these complexes.The use of photolytic demetallation as a means of liberating the modified arene ligands proved to be very successful.The mild conditions, high yields and low cost of the starting iron complexes make this method one of the most general and practical routes to sulphide and sulphone compounds.