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General Description

2-(2-chlorophenylsulfanyl)benzothiazole is a chemical compound with the molecular formula C13H8ClNS2. It is a benzothiazole derivative with a chlorophenylsulfanyl moiety attached to the benzene ring. 2-(2-CHLOROPHENYLSULFANYL)BENZOTHIAZOLE has potential applications in the field of organic synthesis and pharmaceutical research due to its ability to act as a ligand in coordination chemistry and its biological activities. It is also used as an intermediate in the synthesis of dyes, pharmaceuticals, and agrochemicals. Additionally, 2-(2-chlorophenylsulfanyl)benzothiazole has received attention for its antimicrobial and antitumor properties, making it a subject of interest for further study in the search for new therapeutic agents.

Upstream product

• 615-41-8 2-iodochlorobenzene 
• 149-30-4 2-Mercaptobenzothiazole 
• 95-16-9 1,3-Benzothiazole 
• 694-80-4 2-bromo-1-chlorobenzene 
• 137-07-5 2-amino-benzenethiol 
• 7778-70-3 potassium 2-mercaptobenzothiazolate 
• 31121-19-4 bis(2-chlorobenzene)disulfide 

Relevant academic research and scientific papers

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.

New Synthesis and Biological Evaluation of Benzothiazole Derivates as Antifungal Agents

In search of new antifungal agrochemicals that could replace commercially available, aryl-2-mercaptobenzothiazoles were synthesized. They were prepared by two methodologies, using both photostimulated reaction and microwave assisted reaction. These reactions took place without the use of metallic catalyst by a one-pot procedure with excellent yields (70-98%). Synthesized compounds were evaluated for fungal growth inhibition against Botrytis cinerea. Most of the compounds have an excellent antifungal activity, and three of these showed a superior inhibitory effect to commercial fungicide Triadimefon. IC50 values observed for 2-(phenylthio)benzothiazole, 2-(2-chlorophenylthio)benzothiazole, and 2-(3-chlorophenyl thio)benzothiazole were 0.75, 0.69, and 0.65 μg mL-1, respectively.

Novel copper/PEG-400 catalyst systems for chemoselective S- and N-arylation of 2-mercaptobenzothiazole

A novel approach for chemoselective S- and N-arylation of 2-mercaptobenzothiazole was developed by copper/PEG-400 catalyst systems. Copper source and reaction temperature play an important role in this protocol, selective S-arylation of 2-mercaptobenzothiazole was achieved by using CuI/PEG-400/50 °C catalyst system, while selective N-arylation was achieved with CuO/PEG-400/140 °C catalyst system. Both are compatible with a variety of aryl halides and selectively give the desired S- and N-arylation products in good to excellent yields, respectively.

The direct thiolation of benzothiazole catalyzed by copper complex in superbase system

The copper-catalyzed direct thiolation of benzothiazole with iodobenzene and sulfur in superbase system under oxygen atmosphere is reported. The corresponding 2-thio-substituted benzothiazoles were formed in satisfactory yields. Georg Thieme Verlag KG Stu

Copper oxide nanoparticle-catalyzed chalcogenation of the carbon-hydrogen bond in thiazoles: Synthesis of 2-(organochalcogen) thiazoles

We present (homepage: www.ufsm.br) herein the application of copper nanoparticles/dio-rganyl dichalcogenides to promote the synthesis of 2-(organochalcogen)thiazoles via direct carbon-hydro-gen bond activation in thiazoles. A systematic study of the catalytic system revealed that the presence and amount of base played an essential role in this reaction. The results revealed that electron-donating and electron-withdrawing substituents, in the aromat-ic ring bonded to the chalcogen atom of diorganyl di-chalcogenides, required one equiv. of base, while when neutral substituents were present two equiv. of base were needed to deliver the products in similar yields.

Iron-catalyzed S-arylation of thiols with aryl iodides

(Chemical Equation Presented) Strike while the iron is hot: An efficient iron-catalyzed protocol for the S-arylation of aromatic and heteroaromatic thiol derivatives has been developed, which involves an inexpensive catalyst system formed by combining FeCl3 and N,N′-dimethylethylenediamine at 135°C. This method avoids the use of expensive and/or air-sensitive ligands and provides in most cases the desired sulfide in high yields.