1629-93-2

Usage

Uses

Used in Pharmaceutical Industry:
5-Fluoro-2-phenylbenzo[d]thiazole is used as a building block for the synthesis of various biologically active molecules, contributing to drug discovery and development. Its pharmacological activities include antibacterial, antifungal, and anticancer properties, making it a valuable compound for creating new therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical industry, 5-Fluoro-2-phenylbenzo[d]thiazole serves as a building block in the development of compounds with pesticidal properties, helping to create new agrochemical products for crop protection and management.
Used in Chemical Research:
5-Fluoro-2-phenylbenzo[d]thiazole is utilized as a research tool in chemical investigations, aiding scientists in understanding the structure-activity relationships of various organic compounds and exploring new synthetic pathways.
Used as a Precursor in Organic Synthesis:
5-FLUORO-2-PHENYLBENZO[D]THIAZOLE also acts as a precursor in the synthesis of diverse organic compounds, enabling the creation of a wide range of chemical products for various applications across different industries.

InChI:InChI=1/C13H8FNS/c14-10-6-7-12-11(8-10)15-13(16-12)9-4-2-1-3-5-9/h1-8H

Upstream product

• 15111-14-5 2-iodo-N-(phenylmethylene)-benzenamine 
• 100-52-7 benzaldehyde 
• 255724-71-1 5-fluoro-2-iodoaniline 
• 364-77-2 4-fluoro-1-iodo-2-nitrobenzene 
• 345-17-5 1-chloro-4-fluoro-2-nitrobenzene 
• 100-46-9 benzylamine 
• 100-44-7 benzyl chloride 
• 108-88-3 toluene 
• 364-74-9 1,4-difluoro-2-nitrobenzene 
• 103-82-2 phenylacetic acid 
• 1629-15-8 N-(3-fluorophenyl)benzamide 
• 372-19-0 meta-fluoroaniline 
• 98-88-4 benzoyl chloride 
• 98-86-2 acetophenone 

Relevant academic research and scientific papers

Photocatalyst- And Transition-Metal-Free Visible-Light-Promoted Intramolecular C(sp2)-S Formation

A photocatalyst- and transition-metal-free visible-light-induced cyclization of ortho-halothiobenzanilides has been developed. Upon irradiation with visible light, substrates undergo dehalogenative cyclization to 2-aryl benzothiazoles with high efficiency and selectivity. This photocyclization exhibits a high tolerance to various functional groups, is applicable for the synthesis of 2-alkyl benzothiazoles, and is easy to set up for gram-scale reaction.

Method for preparing benzothiazole compound from visible light promoted N-(2-bromophenyl) thioamide

The invention discloses a method for preparing a benzothiazole compound from N-(2-bromophenyl) thioamide under the promotion of visible light. Specifically, under the protection of inert gas, according to the molar ratio of N-(2-bromophenyl) thioamide to inorganic base being 1: 0.5, reactants are added into a reaction container provided with a stirring device, then dimethyl sulfoxide is added, and stirring reaction is carried out for 2-24 hours at room temperature under the irradiation of visible light to obtain the benzothiazole compound. Under the condition of not adding any photosensitizer or transition metal catalyst, sodium phosphate is used as alkali, and under the irradiation of a 45W household compact fluorescent lamp, a series of intramolecular cross-coupling reactions of N-(2-bromophenyl) thioamide are realized. In addition, the benzothiazole compound can be obtained with high yield. The whole process is green, efficient and easy to operate, and the method is a good method for synthesizing the benzothiazole compound.

TBHP/KI-Promoted Annulation of Anilines, Ethers, and Elemental Sulfur: Access to 2-Aryl-, 2-Heteroaryl-, or 2-Alkyl-Substituted Benzothiazoles

An efficient TBHP/KI-promoted annulation of anilines with ethers and elemental sulfur has been developed through the selective C-O bond cleavage of ethers under transition-metal-free conditions. A wide range of 2-aryl-, 2-heteroaryl-, and 2-alkyl-substituted benzothiazoles were easily prepared with satisfactory yields and good functional group compatibility.

Copper-Catalyzed Benzylic C—H Functionalization, Oxidation and Cyclization of Methylarenes: Direct Access to 2-Arylbenzothiazoles

The direct C—H functionalization of methylarenes is of great significance. Herein, a copper-catalyzed oxidative C—N/C—S bond formation through benzylic C(sp3)—H functionalization, oxidation and cyclization of methylarenes is reported. Various 2-arylbenzothiazoles have been synthesized in moderate to excellent yields with readily available o-iodoaniline, potassium sulfide, and methylarenes as raw materials.

Method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions

The invention discloses a method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions. According to the method, glacial aceticacid is taken as a catalyst; at solvent-free room temperature conditions, physical grinding is adopted, reaction of 2-substituted arylamines (2-mercapto arylamine, 2-aminophenol, and o-phenylenediamine) and aromatic aldehydes is carried out using physical grinding. The method is friendly to the environment, is simple in operation, is safe, is low in cost, and is high in efficiency. Compared withthe prior art, the advantages are that: the method is suitable for a large amount of functional groups, yield is high, less by-product is generated, operation is simple, the method is safe, cost is low, and the method is friendly to the environment.

Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer

Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.

Efficient 2-aryl benzothiazole formation from acetophenones, anilines, and elemental sulfur by iodine-catalyzed oxidative C(CO)-C(alkyl) bond cleavage

A novel and efficient iodine-catalyzed one-pot reaction of aromatic amines, acetophenones, and elemental sulfur for the synthesis of 2-aryl benzothiazoles is described. The process involves sequential C?S and C-N bond formation followed by C(CO)?C bond cleavage from readily accessible starting materials. A wide range of functional groups is tolerated under oxidant and metal-free condition and moderate to good product yields are obtained.

Elemental Sulfur-Mediated Decarboxylative Redox Cyclization Reaction: Copper-Catalyzed Synthesis of 2-Substituted Benzothiazoles

A S 8 -mediated directed decarboxylative redox-cyclization strategy for the synthesis of 2-substituted benzothiazoles from o -iodoanilines, arylacetic acids, and elemental sulfur catalyzed by cheap copper metal has been developed. This reaction is operationally simple, ligand-free, compatible with a wide range of functional groups, and provides the desired products in good to excellent yields. In addition, a gram-scale experiment was carried out to furnish PMX 610, an antitumor drug.

The invention relates to a thiourea as the sulfur source synthesis of substituted 2 - aryl benzo thiazole

The invention discloses a method for synthesizing poly-substituted 2-aryl benzothiazoles by utilizing thiourea as a sulphur source. According to the method, thiourea reacts with benzyl chloride to generate an S-benzylisothiourea salt in situ. After that, through the aromatic nucleophilic substitution reaction of the obtained S-benzylisothiourea salt with 2-fluoronitrobenzene and then the one-step reduction (one-pot reaction) process, o-amino phenyl benzyl thioether as an intermediate product can be obtained. Finally, through the iron-catalyzed cross-dehydrogenative-coupling reaction of the o-amino phenyl benzyl thioether, a target product can be obtained. Compared with the traditional synthetic method, the method has the significant advantages of (1) short reaction step, wherein the target product can be synthesized through only three steps of simple reactions by utilizing simple chemical raw materials; (2) mild reaction condition, high atom economy, and relatively safe and cheap reaction reagents; (3) high reaction yield, good substrate tolerance and free of any dangerous or high-toxicity reagent. Therefore, the method might be applied to the large-scale production.

Copper-Catalyzed Arylation of Benzothiazoles with Toluene Derivatives: Synthesis of 2-Arylbenzothiazole

A copper-catalyzed reaction of benzothiazole and readily available toluene derivatives has been disclosed. This protocol is proposed to proceed through the oxidation of toluene and ring opening of benzothiazole, thus providing a new pathway for the synthesis of 2-arylbenzothiazoles..