22868-31-1

Basic information

• Product Name: 2-(3-CHLOROPHENYL)BENZO[D]THIAZOLE
• Synonyms: 2-(3-CHLOROPHENYL)BENZO[D]THIAZOLE;2-(3-Chloro-phenyl)-benzothiazole
• CAS NO: 22868-31-1
• Molecular Formula: C₁₃H₈ClNS
• Molecular Weight: 245.73
• Mol File: 22868-31-1.mol
• Article Data: 86

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(3-CHLOROPHENYL)BENZO[D]THIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-CHLOROPHENYL)BENZO[D]THIAZOLE(22868-31-1)
• EPA Substance Registry System: 2-(3-CHLOROPHENYL)BENZO[D]THIAZOLE(22868-31-1)

Safety Data

• Hazardous Substances Data: 22868-31-1(Hazardous Substances Data)

Usage

Type of compound

Heterocyclic aromatic compound

Structure

Contains a benzene ring fused to a thiazole ring, with a chlorophenyl group attached at the 2-position

Usage

Synthesis of various pharmaceuticals and agrochemicals, potential applications in materials science and organic electronics

Potential properties

Anti-cancer, fluorescent probe for lipid membranes, organic semiconductor in optoelectronic devices.

Upstream product

• 618-46-2 m-Chlorobenzoyl chloride 
• 137-07-5 2-amino-benzenethiol 
• 587-04-2 m-Chlorobenzaldehyde 
• 1141-88-4 2-Aminophenyl disulfide 
• 95-16-9 1,3-Benzothiazole 
• 2039-85-2 3-Chlorostyrene 
• 108-41-8 1-chloro-3-methylbenzene 
• 87707-93-5 2-[(2-Amino-phenylsulfanyl)-(3-chloro-phenyl)-methyl]-malonic acid diethyl ester 
• 26767-07-7 2-(3-chlorophenyl)-2-oxoacetic acid 
• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 4152-90-3 m-chlorobenzylamine 
• 99-02-5 3'-Chloroacetophenone 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 63503-60-6 3-chlorophenylboronic acid 

Downstream Products

• 1316275-52-1 3-[benzothiazole-2-yl]phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1454287-78-5 (2-(benzo[d]thiazol-2-yl)-4-chlorophenyl)(phenyl)methanone 
• 1440999-88-1 2-(benzo[d]thiazol-2-yl)-4-chlorophenyl acetate 
• 1440999-89-2 C₁₇H₁₂ClNO₄S 
• 1379479-47-6 2-(4-chloro-4'-methoxy-[1,1'-biphenyl]-2-yl)benzo[d]thiazole 
• 1379479-48-7 2-(4,4'-dichloro-[1,1'-biphenyl]-2-yl)benzo[d]thiazole 
• 1379479-46-5 2-(4-chloro-[1,1'-biphenyl]-2-yl)benzo[d]thiazole 

Relevant articles and documents

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).

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.

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.