1629-07-8

Usage

Uses

Used in Pharmaceutical Industry:
2-(3-Fluorophenyl)-1,3-benzothiazole serves as an intermediate in the synthesis of potential drugs and bioactive compounds. Its unique structure allows it to be a valuable component in the development of new pharmaceutical agents, potentially leading to advancements in medicinal chemistry.
Used in Materials Science:
In the field of materials science, 2-(3-Fluorophenyl)-1,3-benzothiazole may find applications due to its specific chemical and physical properties. Its incorporation into materials could enhance their performance or introduce new functionalities, depending on the requirements of various applications.
Used in Organic Synthesis:
As a benzothiazole derivative, 2-(3-Fluorophenyl)-1,3-benzothiazole is utilized in organic synthesis for the creation of a variety of organic compounds. Its presence can influence the reactivity and selectivity of synthetic reactions, making it a useful building block in organic chemistry.
2-(3-Fluorophenyl)-1,3-benzothiazole holds promise for further research and development across different domains, given its distinctive molecular architecture and the potential for it to exhibit biological activities that could be harnessed in various applications.

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

Upstream product

• 2516-40-7 2-bromo-1,3-benzothiazole 
• 768-35-4 3-fluorophenylboronic acid 
• 95-16-9 1,3-Benzothiazole 
• 1121-86-4 1-Fluoro-3-iodobenzene 
• 350-51-6 3-fluorostyrene 
• 574719-67-8 3-fluoro-N-(2-bromophenyl)benzamide 
• 615-36-1 2-bromoaniline 
• 79477-87-5 2-(3-fluorophenyl)-2-oxoacetic acid 
• 137-07-5 2-amino-benzenethiol 
• 1629-18-1 3-fluoro-N-phenylbenzothioamide 
• 1711-07-5 3-fluorobenzoyl chloride 
• 62-53-3 aniline 
• 1629-09-0 3-fluoro-N-phenylbenzamide 
• 352-70-5 m-Fluorotoluene 

Downstream Products

• 90481-42-8 2-(benzo[d]thiazol-2-yl)-4-fluoro-phenol 

Relevant academic research and scientific papers

α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water

A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).

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.

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

Photoinduced Heterogeneous C?H Arylation by a Reusable Hybrid Copper Catalyst

Heterogeneous copper catalysis enabled photoinduced C?H arylations under exceedingly mild conditions at room temperature. The versatile hybrid copper catalyst provided step-economical access to arylated heteroarenes, terpenes and alkaloid natural products with various aryl halides. The hybrid copper catalyst could be reused without significant loss of catalytic efficacy. Detailed studies in terms of TEM, HRTEM and XPS analysis of the hybrid copper catalyst, among others, supported its outstanding stability and reusability.

Aerobic oxidative synthesis of quinazolinones and benzothiazoles in the presence of laccase/DDQ as a bioinspired cooperative catalytic system under mild conditions

The current study applied laccase/DDQ as a bioinspired cooperative catalytic system for the synthesis of quinazolinones (80-95% yield) and benzothiazoles (65-98% yield) using air or O2 as ideal oxidants in aqueous media at ambient temperature. The aerobic oxidative cyclization reactions occur in two steps: (i) chemical cyclization; (ii) chemoenzymatic oxidation. These methods are more environment-friendly, efficient, simple and practical than other reported methods due to the use of O2 as an oxidant, laccase as an eco-friendly biocatalyst, aqueous media as the solvent and free from any toxic transition metal and halide catalysts. Therefore, these methods can be applied in pharmaceutical and other sensitive synthetic procedures.

Preparation method of 2-substituted benzothiazole

The invention discloses a preparation method of 2-substituted benzothiazole, and belongs to the field of organic chemical synthesis. The preparation method of the 2-substituted benzothiazole specifically comprises the following steps: by taking an N-aryl thioamide compound as a raw material and taking graphite-phase carbon nitride (g-C3N4) prepared by urea thermal polymerization condensation as aphotocatalyst, carrying out a cyclization reaction under a mild condition to prepare the 2-substituted benzothiazole. The method has the advantages of simple operation, cheap and easily available catalyst, mild reaction conditions, wide substrate application range, no strong oxidant and no metal residue, and provides an economical, practical, green and environment-friendly new method for synthesisof 2-substituted benzothiazole widely applied to the fields of medicines, dyes, pesticides and the like.

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.

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.

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.