2786-51-8

Usage

Uses

Used in Pharmaceutical Industry:
5-Chlorobenzo[d]thiazole is used as a key intermediate in the synthesis of hydroxyl alkylation derivatives of benzothiazole. These derivatives are valuable compounds in the development of pharmaceuticals, particularly in the design of novel drugs with potential therapeutic applications. The presence of the chlorine atom and the thiazole ring in 5-chlorobenzo[d]thiazole allows for the formation of diverse chemical structures, which can be further modified to create new drug candidates with improved pharmacological properties.
Used in Chemical Synthesis:
In addition to its applications in the pharmaceutical industry, 5-chlorobenzo[d]thiazole is also used as a versatile building block in the synthesis of various organic compounds. Its unique structure allows for the formation of a wide range of chemical derivatives, which can be employed in different chemical reactions to produce a variety of products. This makes 5-chlorobenzo[d]thiazole a valuable starting material for the synthesis of complex organic molecules, including dyes, pigments, and other specialty chemicals.
Used in Material Science:
5-Chlorobenzo[d]thiazole and its derivatives have also found applications in the field of material science. The unique electronic and structural properties of 5-CHLOROBENZOTHIAZOLE make it suitable for the development of new materials with specific properties, such as conductivity, stability, and reactivity. For example, 5-chlorobenzo[d]thiazole can be used in the synthesis of organic semiconductors, which have potential applications in electronic devices, sensors, and energy storage systems.

Upstream product

• 5331-91-9 5-chloro-1,3-benzothiazole-2(3H)-thione 
• 2565-30-2 formyl chloride 
• 615-48-5 2-amino-4-chloro-benzenethiol hydrochloride 
• 5331-91-9 5-chloro-2-mercaptobenzothiazole 
• 64-18-6 formic acid 
• 89-61-2 2,5-dichloronitrobenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 1004-00-8 4-chloro-2-aminobenzenethiol 
• 6828-35-9 5-chloro-2-iodoaniline 
• 67-68-5 dimethyl sulfoxide 
• 122-51-0 orthoformic acid triethyl ester 
• 36776-27-9 4-chloro-2-nitro-thiophenol 
• 298-12-4 Glyoxilic acid 
• 124-38-9 carbon dioxide 

Downstream Products

• 2898-96-6 5-chloro-3-methyl-benzothiazolium; toluene-4-sulfonate 
• 149474-18-0 5-(2'-Carboxyphenylamino)benzothiazole 
• 3479-10-5 1-amino-3-chlorobenzene-6-sulfonic acid 
• 1388625-42-0 2-(5-chlorobenzothiazol-2-yl)-5-phenyloxazole 
• 1443355-98-3 5-chloro-2-o-chlorophenylsulfanylbenzothiazole 
• 1443356-09-9 5-chloro-2-m-chlorophenylsulfanylbenzothiazole 
• 1443356-13-5 5-chloro-2-p-fluorophenylsulfanylbenzothiazole 
• 17485-31-3 5-chloro-2-(2-chlorophenyl)benzothiazole 
• 32729-67-2 (5-chloro-1,3-benzothiazol)-2-yl(phenyl)methanone 
• 92-39-7 2-chlorophenothiazine 

Relevant academic research and scientific papers

Hydrosilane-promoted cyclization of 2-aminothiophenols by CO2to benzothiazoles

A new route is presented to synthesize benzothiazoles via cyclization of 2-aminothiophenols by CO2 in the presence of diethylsilane catalyzed by 1,5-diazabicyclo[4.3.0]non-5-ene, and a series of benzothiazoles were obtained in good yields.

Design, synthesis and biological evaluation of benz-fused five-membered heterocyclic compounds as tubulin polymerization inhibitors with anticancer activities

A series of benz-fused five-membered heterocyclic compounds were designed and synthesized as novel tubulin inhibitors targeting the colchicine binding site. Among them, compound 4d displayed the highest antiproliferative activity against four cancer cell lines with an IC50 value of 4.9?μM in B16-F10 cells. Compound 4d effectively inhibited tubulin polymerization in vitro (IC50 of 13.1?μM). Further, 4d induced cell cycle arrest in G2/M phase. Finally, 4d inhibited the migration of cancer cells in a dose-dependent manner. In summary, these results suggest that compound 4d represents a new class of tubulin inhibitors deserving further investigation.

Synthesis method of benzothiazole compound

The invention relates to a novel process for synthesizing benzothiazole compounds, which comprises the following steps of: (1) heating and stirring orthoester, o-aminothiophenol and derivatives thereof to react, monitoring the reaction process by TLC, and obtaining crude benzothiazole compounds after the reaction is finished; and (2) distilling the crude benzothiazole compound obtained in the step (1) or recrystallizing by using a solvent, and filtering to obtain the benzothiazole compound. According to the method, no solvent is added in the reaction process, the separation and purification process is optimized, and green production of fine chemicals is effectively achieved; and no catalyst is added, the operation is simple, the reaction time is remarkably shortened, the production efficiency of the product is improved, and the yield can reach 79%-90%. The problems of environmental pollution, potential safety hazards, harm to human health, resource waste and the like caused by the solvent are fundamentally solved, and the method has extremely high green industrialization value.

Synthesis of Benzothiazoles via Photooxidative Decarboxylation of α-Keto Acids

Herein, synthesis of benzothiazoles via decarboxylative cross-coupling between α-keto acids and 2-aminothiophenols under blue LED irradiation without using any photocatalyst or metal at room temperature is described. The formation of benzothiazole is driven by the EDA (electron donor-acceptor) complex formed between α-keto acid and 2-aminothiophenol. This methodology gives easy access to 2-substituted and -unsubstituted benzothiazoles in moderate to good yields. α-Keto acids and 2-aminothiophenols bearing different functional groups were easily transformed under the given conditions. (Figure presented.).

K2S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2-Unsubstituted Benzothiazoles

We describe a three-component reaction of o-iodoanilines with K2S and DMSO that provides 2-unsubstituted benzothiazoles in moderate to good isolated yields with good functional group tolerance. Electron-rich aromatic amines and o-phenylenediamines instead of o-iodoanilines provided 2-unsubstituted benzothiazoles and 2-unsubstituted benzimidazoles with and without K2S under similar conditions. Notably, DMSO plays three vital roles: carbon source, solvent, and oxidant.

Synthetic method of ammonium acetate-mediated benzothiazole compound

The invention discloses a synthetic method of an ammonium acetate-mediated benzothiazole compound . The synthetic method comprises the steps: adding an o-haloaniline derivative, potassium sulfide, dimethyl sulfoxide, a catalyst, an additive 1 and an additive 2 into a reaction tube, carrying out a stirring reaction at the temperature of 130-150 DEG C, cooling to room temperature after the reactionis finished, and separating and purifying the product to obtain the benzothiazole compound. The invention provides the synthetic method of the benzothiazole compound by taking K2S as a sulfur source,DMSO as a carbon source and an oxidizing agent, an o-haloaniline derivative as a substrate and an ammonium acetate mediated three-component one-pot method. The method has the advantages of fewer reaction steps, mild reaction conditions, good functional group tolerance and the like.

Method for synthesizing benzothiazole by microwave radiation of benzothioamide compound in aqueous phase

The invention discloses a method for synthesizing benzothiazole by microwave radiation of a benzothioamide compound in an aqueous phase. The method includes the steps: adding the benzothioamide compound into the aqueous phase under microwave conditions; performing cyclization under alkaline conditions to generate the benzothiazole. The method for preparing the benzothiazole is environmentally friendly, simple and convenient in operation, safe, cheap and efficient. Compared with the prior art, the method is applicable to a lot of functional groups, high in yield, few in by-products, simple in operation, safe, low in cost and environmentally friendly.

Atmospheric CO2 promoted synthesis of N-containing heterocycles over B(C6F5)3 catalyst

B(C6F5)3 combined with atmospheric CO2 was found to be highly effective for the cyclization of ortho-substituted aniline derivatives with N,N-dimethylformamide (DMF), and a series of N-containing heterocycles including benzothiazoles, benzimidazoles, quinazolinone and benzoxazole were obtained in good to excellent yields.

Ionic Liquid-Catalyzed C-S Bond Construction using CO2 as a C1 Building Block under Mild Conditions: A Metal-Free Route to Synthesis of Benzothiazoles

The construction of the C-S bond using CO2 as a C1 feedstock can be considered as a green route for the synthesis of S-containing compounds and is of great significance. Herein, we report the acetate-based ionic liquids (ILs)-catalyzed synthesis of benzothiazoles via cyclization of 2-aminothiophenols with CO2 and hydrosilane under mild conditions (e.g., 60 °C, 0.5 MPa). It was found that the IL (e.g., 1-butyl-3-methylimidazolium acetate, [Bmim][OAc]) served as a multifunctional catalyst with activating CO2 and hydrosilane to form a formoxysilane intermediate, as well as simultaneously activating 2-aminothiophenols through a hydrogen bond, finally resulting in the production of benzothiazoles. [Bmim][OAc] showed the best performance, and a series of benzothiazoles were obtained in high yields. To the best of our knowledge, this is the first protocol for the synthesis of benzothiazoles using CO2 as a C1 building block under metal-free and mild conditions.

NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles

The pair NaBH4-TMEDA as hydride source and a palladium catalyst in THF prove to be an efficient system for the hydrodehalogenation of halogenated heterocycles with one or more heteroatoms. In general, Pd(OAc) 2-PPh3 rapidly hydrodehalogenates reactive halo-heterocycles such as bromo-pyridines, -quinolines, -thiophenes, -indoles, -imidazoles, etc., at room temperature in very good yields, whereas in most cases PdCl2(dppf) reduces less reactive halides such as chloro-pyridines, -quinolines, -pyrimidines and bromo-indoles, -benzofurans, etc. Moreover, PdCl2(tbpf) shows to be even more active removing the 2- and 5-chlorine from both thiophene and thiazole rings. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene and nitrile substituents. Moreover, with a proper selection of the catalyst it is also possible to obtain a good control in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.