6265-97-0

Usage

Type of compound

Phenolic compound

Contains

Benzothiazolyl group and chlorophenol group

Common uses

Fungicide, bactericide, wood preservation, biocide in water treatment

Antimicrobial properties

Strong

Toxicity

Toxic to aquatic life, may pose health hazards if not properly handled

InChI:InChI=1/C13H8ClNOS/c14-8-5-6-11(16)9(7-8)13-15-10-3-1-2-4-12(10)17-13/h1-7,15H/b13-9+

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 137-07-5 2-amino-benzenethiol 
• 635-93-8 5-chlorosalicyclaldehyde 
• 321-14-2 5-chloro-2-hydroxybenzoic acid 

Relevant academic research and scientific papers

A novel colorimetric and ratiometric fluorescence probe based on ‘C-CN’ for detection of hydrazine and its imaging in living cells and mouse

Hydrazine plays an important role in chemistry, pharmaceuticals, agriculture and aerospace. However, it is not to be underestimated and has been identified as harmful to the human body. Therefore, it is significant and urgent to develop the detection of h

A reversible vapor-responsive fluorochromic molecular platform based on coupled AIE–ESIPT mechanisms and its applications in anti-counterfeiting measures

In this work, a series of 2-(2-hydroxyphenyl)benzothiazole (HBT) derivatives with an aggregation-induced emission–excited state intramolecular proton transfer (AIE-ESIPT) dual mechanism was synthesized. We systematically investigated their optical properties in solution, aqueous suspension, and the solid state. The fluorescence properties of these five compounds were highly dependent on the solvent environment. Particularly, DMSO and DMF were found to significantly promote deprotonation of the phenolic hydroxyl and favor fluorescence emission from the phenolic anion. The Keto or Enol forms generally could be transformed to phenolic anions with the aid of base in solution. The results from aggregation-induced emission enhancement (AIEE) and red-shifted AIE clearly illustrated the evolution process of the fluorescence spectra, indicating that the three luminescent species in the solution were transformable. The systematic investigation demonstrated that the desired fluorescence could be generated for HBT derivatives by varying the solvents or adding additives, such as base or water, to the solution. Because of the synergistic effect of AIE and ESIPT, these fluorophores exhibited high solid-state quantum yields and large Stokes shifts. These dyes also featured high photostability and tunable emission spectra covering most of the visible light region. Single crystal studies and theoretical calculations elucidated the luminescent properties. When loaded on filter paper, the HBT-based dyes exhibited high-efficiency fluorescence visualization and reversible solid-state luminescence switching under alternating amine and acid vapor treatments. These dyes were used on banknotes for anti-counterfeiting measures, demonstrating the practical applications of these molecules as security inks.

Highly efficient AgNO3-catalyzed approach to 2-(benzo[d]azol-2-yl)phenols from salicylaldehydes with 2-aminothiophenol, 2-aminophenol and benzene-1,2-diamine

A new, convenient and efficient AgNO3-catalyzed strategy for the preparation of 2-(benzo[d]azol-2-yl)phenol derivatives in good to excellent yields (63–98%) is described. The reaction proceeds via condensation/intramolecular nucleophilic addition/oxidation process between substituted salicylaldehydes and 2-aminothiophenol, 2-aminophenol or benzene-1,2-diamine under mild reaction conditions. Notably, this reaction utilizes cheap AgNO3 as a readily available and low-cost benign oxidant at low catalyst loadings with excellent functional group tolerance.

Unified synthesis of mono/bis-arylated phenols via RhIII-catalyzed dehydrogenative coupling

2,6-Bis-arylated phenols are rarely reported and are synthetically challenging. Directed C-H functionalization reactions, using a directing group (DG), might provide a convenient solution to their synthesis. However, this strategy usually results in partial cleavage of the directing group, preventing further/second C-H activation cascades. Herein we report a general strategy that allows for the precise control of the oxidation pathways so that directing groups can be either preserved or cleaved. We found that N-phenoxyacetamides could undergo ortho-arylation reactions with or without an external oxidant, yielding products with different oxidation states, notably the rare bis-arylated phenols. Notably, a unique rhodacycle intermediate was isolated, characterized by X-ray crystallography, and confirmed to be an active catalyst. Switching between internal and external oxidation could be a general strategy in diverse directed C-H functionalization reactions to realize bis-functionalized products.

The immunomodulation potential of the synthetic derivatives of benzothiazoles: Implications in immune system disorders through in vitro and in silico studies

Benzothiazole and its natural or synthetic derivatives have been used as precursors for several pharmacological agents for neuroprotective, anti-bacterial, and anti-allergic activities. The objecctive of the present study was to evaluate effects of benzot

Antileishmanial activities of benzothiazole derivatives

Benzothiazole derivatives 1-22 were synthesized from 2-aminothiophenol and all synthetic compounds were screened for in vitro antileishmanial activity. These compound showed different types activities against leishmania with IC50 values ranging

IMMUNOSUPPRESSIVE COMPOUNDS

The invention feature series of benzothiazole derivatives as potent immunosuppressive and antiinflammatory agents. Eight compounds 2, 4, 5, 8, 9, 10, 12, and 18 showed potent inhibitory activity on PHA-activated T-cell proliferation. Compounds 2, 4, 8, and 18 were found to have a potent inhibitory activity with IC50 values ranging 50 values 1.9, 5050), respectively.

A robust one-pot synthesis of benzothiazoles from carboxylic acids including examples with hydroxyl and amino substituents

The cyclocondensation of 2-aminothiophenol and carboxylic acids to give benzothiazoles has been carried out under mild conditions using tetrabutylammonium bromide (TBAB) as the reaction medium and triphenyl phosphite as the catalyst. Shorter reaction times, rapid isolation of the products, and excellent yields are advantages of this method. The reaction is found to be general and quite tolerant to the nature of the substituted carboxylic acids.

Synthesis of novel inhibitors of β-glucuronidase based on benzothiazole skeleton and study of their binding affinity by molecular docking

Benzothiazole derivatives 1-26 have been synthesized and their in vitro β-glucuronidase potential has been evaluated. Compounds 4 (IC50 = 8.9 ± 0.25 μM), 5 (IC50 = 36.1 ± 1.80 μM), 8 (IC50 = 8.9 ± 0.38 μM), 13 (IC50/

Syntheses, characterization, and ethylene polymerization of titanium and zirconium complexes with [N, O] ligands

Bidentate monoanionic ligands 2-(benzo[d]thiazol-2-yl) phenol (La), 2-(benzo[d]thiazol-2-yl)-6-methylphenol (Lb), 2-(benzo[d]thiazol-2-yl)-6-tert- butyl-4-methylphenol (Lc), 2-(benzo[d]thiazol-2-yl)-6-chlorophenol (Ld), and 2-(benzo[d]thiazol-2-yl)-4-chlorophenol (Le) have been synthesized. Reactions of TiCl4(THF)2 or ZrCl4 with La-Le afford the corresponding titanium complexes Ti[ON]2RCl2 [R = 6-Me (2b); R = 4-Me-6-But (2c)], and zirconium complexes Zr[ON]2RCl2 [R = H (3a); R = 6-Me (3b); R = 4-Me-6-But (3c); R = 6-Cl (3d); R = 4-Cl (3e)], and Zr[ON R]HCl4·THF [R = 6-Me (4b)], respectively. Complexes 2a-4b were characterized by IR, 1H NMR spectra and elemental analysis. The molecular structures of La, 2b, 2c, 3b, 3c and 4b have been characterized by single-crystal X-ray diffraction analyses. The effect of steric hindrance and the coordination metal on the structure of the products has been investigated. When activated by excess methylaluminoxane (MAO), 2b and 2c, 3a-3e and 4b can be used as catalysts for ethylene polymerization and exhibit moderate to good activities.