39544-83-7

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 59919-17-4 α-(p-chlorophenylthio)isobutyrophenone 
• 637-87-6 1-Chloro-4-iodobenzene 
• 149-30-4 2-Mercaptobenzothiazole 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 106-39-8 bromochlorobenzene 
• 137-07-5 2-amino-benzenethiol 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 106-54-7 p-Chlorothiophenol 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 919867-38-2 4-chlorophenyl 1H-benzo[d][1,2,3]triazole-1-carbodithioate 
• 34220-01-4 di-(4-chlorophenyl)iodonium chloride 

Downstream Products

• 6078-99-5 4-chlorophenyl diethyldithiophosphinate 
• 5745-35-7 p-chlorophenyl dimethyldithiophosphinate 

Relevant academic research and scientific papers

Cross-coupling reaction of organoalane reagents with 2-mercaptobenzo-5-membered heterocycles for efficient synthesis of benzo-5-membered heterocycle sulfides

A highly efficient and simple route for the synthesis of benzo-5-membered heterocycles sulfides has been developed by the cross-coupling reaction of 2-mercaptobenzo-5-membered heterocycles with (hetero)arylaluminum reagents. Various benzo-5-membered heter

Pd/PTABS: Low-Temperature Thioetherification of Chloro(hetero)arenes

The thioetherification of heteroaryl chlorides is an essential synthetic methodology that provides access to bioactive drugs and agrochemicals. Due to their (actual or potential) industrial importance, the development of efficient and low-temperature protocols for accessing these compounds is a requirement for economic and ecologic reasons. A particular highly effective catalytic protocol using the Pd/PTABS system at only 50 °C was developed accordingly. The coupling between chloroheteroarenes and a variety of less reactive arylthiols and alkylthiols was carried out with a high efficiency. Heteroarenes of commercial relevance such as purines and pyrimidines were also found to be useful substrates for the reported transformation. The commercial drug Imuran (azathioprine) was synthesized as an example, and its preparation could be optimized. DFT studies were performed to understand the electronic effects of the tested ligands on the catalytic reaction.

HFIP Promoted Low-Temperature SNAr of Chloroheteroarenes Using Thiols and Amines

A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base-free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.

Copper(I)-Catalyzed Tandem One-Pot Synthesis of 2-Arylthiobenzothiazoles and 2-Arylthiobenzoxazoles in Water

An efficient tandem process for the preparation of 2-arylthiobenzothiazoles has been developed. By condensation of 2-aminobenzenethiol with tetramethylthiuram disulfide (TMTD), 2-mercaptobenzothiazoles was in situ generated, which susequently underwent coupling with iodobenzenes to give the desired 2-arylthiobenzothiazoles fluently in a one-pot manner. This method can also be used for the synthesis of 2-arylthiobenzoxazoles. Inexpensive metal catalyst and ligand, mild reaction temperature, and water as solvent make this protocol practically valuable and useful in organic synthesis.

Disulfide Bond-Containing Ajoene Analogues As Novel Quorum Sensing Inhibitors of Pseudomonas aeruginosa

Since its discovery 22 years ago, the bacterial cell-to-cell communication system, termed quorum sensing (QS), has shown potential as antipathogenic target. Previous studies reported that ajoene from garlic inhibits QS in opportunistic human pathogen Pseudomonas aeruginosa. In this study, screening of an in-house compound library revealed two sulfur-containing compounds which possess structural resemblance with ajoene and inhibit QS in bioreporter assay. Following a quantitative structure-activity relationship (SAR) study, 25 disulfide bond-containing analogues were synthesized and tested for QS inhibition activities. SAR study indicated that the allyl group could be replaced with other substituents, with the most active being benzothiazole derivative (IC50 = 0.56 μM). The compounds were able to reduce QS-regulated virulence factors (elastase, rhamnolipid, and pyocyanin) and successfully inhibit P. aeruginosa infection in murine model of implant-associated infection. Altogether, the QS inhibition activity of the synthesized compounds is encouraging for further exploration of novel analogues in antimicrobial drug development.

Transition-Metal-Free and Oxidant-Free Cross-Coupling of Arylhydrazines with Disulfides: Base-Promoted Synthesis of Unsymmetrical Aryl Sulfides

A novel synthesis of unsymmetrical aryl sulfides, which requires no transition metal catalyst and no oxidant, was developed. This base-promoted cross-coupling reaction proceeded using arylhydrazines and 1 equiv amount of disulfides under inert gas conditions to afford the unsymmetrical aryl sulfides in good yields.

Photo-induced copper-catalyzed C-H chalcogenation of azoles at room temperature

Inexpensive copper catalysts enabled direct C-H chalcogenations at ambient temperature by means of photo-induced catalysis. The expedient copper catalysis set the stage for C-S and C-Se bond formation from readily accessible non-volatile elemental chalcogens. The photo-assisted copper catalysis manifold proved suitable for a wide range of substrates with good functional group tolerance and exhibited high catalytic efficacy even at a reaction temperature of 25 °C.

Synthesis of 2- N / S / C -substituted benzothiazoles via intramolecular cyclative cleavage of benzotriazole ring

The synthesis of numerous 2-N/S/C-substituted benzothiazoles was achieved from substituted thiocarbonylbenzotriazoles via free-radical intramolecular cyclative cleavage of the benzotriazole ring in the presence of (TMS) 3SiH and AIBN under mild

Synthesis of heteroaryl containing sulfides via enaminone ligand assisted, copper-catalyzed C-S coupling reactions of heteroaryl thiols and aryl halides

The C-S cross coupling reactions between electron deficient heteroaryl thiols and aryl halides have been smoothly performed to provide various heteroaryl containing sulfides in the presence of copper catalyst and enaminone ligand. the Partner Organisations 2014.

Efficient C-S cross-coupling of thiols with aryl iodides catalyzed by Cu(OAc)2·H2O and 2,2′-biimidazole

The classical Ullmann C-S cross coupling reaction of aryl iodides with aromatic/alkyl thiols under catalysis of 15 mol% Cu(OAc)2· H2O and 15 mol% 2,2′-biimidazole works at 80°C in DMSO for 3 h to provide a variety of aryl sulfides in good to excellent yields. The classical Ullmann C-S cross coupling reaction of aryl iodides with aromatic/alkyl thiols under catalysis of 15 mol% Cu(OAc)2· H2O and 15 mol% 2,2′-biimidazole works at 80°C in DMSO for 3 h to provide a variety of aryl sulfides in good to excellent yields. Copyright