952-16-9

Usage

Uses

Used in Pharmaceutical Industry:
5-CHLORO-2-PHENYLBENZO[D]THIAZOLE is used as a pharmaceutical intermediate for the development of drugs with antimicrobial, antifungal, and anticancer properties. Its unique chemical structure allows it to target specific biological pathways, making it a promising candidate for the treatment of various diseases.
Used in Agrochemical Industry:
In the agrochemical industry, 5-CHLORO-2-PHENYLBENZO[D]THIAZOLE is used as an active ingredient in the formulation of pesticides and fungicides. Its antimicrobial and antifungal properties help protect crops from various pathogens, ensuring higher yields and better crop quality.
Used in Organic Synthesis:
5-CHLORO-2-PHENYLBENZO[D]THIAZOLE is used as a building block in the synthesis of complex organic molecules. Its versatile chemical structure allows for various chemical reactions, enabling the creation of a wide range of compounds with different properties and applications.
Used in Specialty Chemicals and Materials Production:
5-CHLORO-2-PHENYLBENZO[D]THIAZOLE is used as an important intermediate in the production of specialty chemicals and materials. Its unique properties and reactivity make it suitable for the development of advanced materials with specific characteristics, such as high thermal stability, electrical conductivity, or optical properties.

InChI:InChI=1/C13H8ClNS/c14-10-6-7-12-11(8-10)15-13(16-12)9-4-2-1-3-5-9/h1-8H

Upstream product

• 60-29-7 diethyl ether 
• 873984-43-1 benzoic acid-(5-chloro-2-mercapto-anilide) 
• 64-17-5 ethanol 
• 74462-18-3 2-benziltio-5-cloroanilina 
• 855294-59-6 thiobenzoic acid S-(4-chloro-2-nitro-phenyl ester) 
• 615-48-5 2-amino-4-chloro-benzenethiol hydrochloride 
• 98-88-4 benzoyl chloride 
• 2050-66-0 bis(2-nitro-4-chlorophenyl)disulfide 
• 100-47-0 benzonitrile 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 1004-00-8 4-chloro-2-aminobenzenethiol 
• 6004-21-3 3'-chloro-benzanilide 
• 100-52-7 benzaldehyde 
• 618-31-5 benzylidene dibromide 

Downstream Products

• 854084-74-5 5-chloro-6-nitro-2-phenyl-benzothiazole 
• 854058-96-1 5-chloro-2-phenyl-benzothiazol-6-ylamine 

Relevant academic research and scientific papers

Delivering 2-Aryl Benzoxazoles through Metal-Free and Redox-Neutral De-CF3Process

An unexpected cleavage of the Csp3-CF3 bond of CF3-hydrobenzoxazoles has been disclosed, affording a range of 2-aryl benzoxazoles under metal-free and redox-neutral conditions. This transformation has demonstrated broad substrate scope and good compatibility of functional groups. 2-Aryl benzothiazole and 2-aryl benzoimidazole could be smoothly assembled in the same manner. On the basis of preliminary mechanistic studies, base initiated and aromatization driven β-carbon elimination was considered to be the key step for the formation of 2. This reaction offers an alternative, facile, and sustainable route to access important 2-aryl benzoxazole motifs.

Sulfur-Promoted Redox Cyclization of 2,2′-Dinitrodiphenyl Disulfides and Benzylamines

This study aims to develop green and sustainable advanced synthetic methods based on redox cyclization. Elemental sulfur is shown to promote the efficient synthesis of 2-substituted benzothiazoles from 2,2′-dinitrodiphenyl disulfides and benzylamines via redox cyclization in the absence of transition-metal catalysts and solvents. The 2-substituted benzothiazoles are obtained in good to excellent yields. This synthetic methodology is highly atom-economical and does not require any external oxidizing and/or reducing agents.

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).

Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation

We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.

ZnO-NPs catalyzed condensation of 2-aminothiophenol and aryl/alkyl nitriles: Efficient green synthesis of 2-substituted benzothiazoles

The synthesis of 2-substituted benzothiazoles has been described using ZnO-nanoparticles as a catalyst. The condensation of 2-aminothiophenol and aryl/alkyl nitriles resulted in the formation of various 2-substituted benzothiazoles under solvent-free reaction conditions. The library of 2-substituted benzothiazoles has been synthesized in good to excellent yield. The reaction has shown a wide range of functional group compatibility for both varyingly substituted 2-aminothiophenols and nitriles. The protocol has many advantages such as faster reaction rate, mild reaction conditions, various functional group compatibility, excellent yield, solvent-free reaction conditions, easy recovery of materials, and excellent catalyst recyclability, among others. The various advantages of this protocol make it a more feasible, economical, and environmentally benign process.

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.

Oxidant/Solvent-Controlled I2-Catalyzed Domino Annulation for Selective Synthesis of 2-Aroylbenzothiazoles and 2-Arylbenzothiazoles under Metal-Free Conditions

A simple and practical domino protocol for the selective synthesis of 2-aroylbenzothiazoles and 2-aryl benzothiazoles catalyzed by I2 is developed under metal-free conditions. The reaction outcomes are exclusively controlled by the reaction oxidant/medium. With DMSO employed as both the solvent and the oxidant, an oxidation of aromatic methyl ketones takes precedence over the condensation with 2-aminobenzenethiols. On the other hand, when the reaction was carried out in PhNO2 or in 1,4-dioxane containing PhNO2, the condensation of aromatic methyl ketones with 2-aminobenzenethiols has priority to form imines which is followed by an oxidation of the methyl group from ketones to afford 2-arylbenzothiazoles as a sole product. The PhNO2/I2 co-catalytic system is proposed first time.

Ultrasound-assisted efficient and green synthesis of 2-substituted benzothiazoles under solvent-free condition using recyclable sulfated tungstate

Sulfated tungstate catalyzed an efficient and ecofriendly protocol has been described for the synthesis of 2-substituted benzothiazoles. The corresponding benzothiazoles were obtained using a condensation reaction of 2-aminothiophenol with various aldehydes under ultrasound irradiation at room temperature. Various functional groups on the 2-aminothiophenol as well as on the aldehydes were tolerated to provide 2-substituted benzothiazoles derivatives in excellent yields. The faster reaction rate, solvent-free or mild reaction conditions, wide functional group compatibility, excellent yields, easy work-up procedure, and excellent catalyst recyclability are the advantages of this protocol. These advantages make this process more practicable, cost-effective, and environmentally benign.

Urea nitrate–catalyzed C-N and C-S bond formation: A mechanochemical approach for 5-chloro-2-arylbenzo[d]thiazole derivatives

A series of substituted 5-chloro-2-arylbenzo[d]thiazoles were synthesized using 4-chloro-2-aminothiophenol and aromatic aldehydes in the presence of urea nitrate as a catalyst using the mechanochemical grindstone technique. This protocol was effectively carried out under metal-free conditions at room temperature, and the desired products were obtained in high to excellent yields in short reaction time (30–60 s). The structure of all the synthesized derivatives was confirmed by spectral characterization. The designed protocol has several benefits like eco-friendly, solvent-free, high yields, easy workup, and recyclability of catalyst. The catalyst was reusable at least four times without significant loss of activity. The good functional group tolerance with a series of derivatives has been demonstrated.

Synthesis of benzothiazoles using fluorescein as an efficient photocatalyst under visible light

This work reports a novel and efficient method for the synthesis of benzothiazoles using 2-aminothiophenol derivatives in conjunction with aromatic aldehyde as starting materials via visible-light-induced condensation cyclization. Utilizing fluorescein as the photocatalyst and blue LED lamp as the light source, the reaction proceeds in the presence of a molecular oxygen atmosphere without the need for metal catalyst or an additional oxidant. Significantly, this method exhibits good tolerance in substrates, and a variety of 2-aminothiophenol derivatives and aromatic aldehyde are amenable to producing the corresponding benzothiazoles in high to excellent yields.