31224-76-7

Usage

Uses

Used in Chemical Intermediates:
Benzothiazole, 2-(1H-indol-3-yl)-, is utilized as a chemical intermediate in the synthesis of various products, including dyes, pharmaceuticals, and rubber accelerators. Its unique structure allows it to serve as a building block for the development of complex organic molecules.
Used in Organic Electronics and Optoelectronics:
Due to its electronic properties, Benzothiazole, 2-(1H-indol-3-yl)-, has potential applications in the field of organic electronics and optoelectronics. It can be incorporated into the design of electronic devices such as organic light-emitting diodes (OLEDs) and organic solar cells, where its properties may enhance performance or enable new functionalities.
Used in Pharmaceutical Industry:
Benzothiazole, 2-(1H-indol-3-yl)-, has been studied for its potential biological and pharmacological activities. It is particularly noted for its anti-cancer properties, where it may contribute to the development of new therapeutic agents targeting various types of cancer.
Used in Anti-fungal Applications:
Additionally, Benzothiazole, 2-(1H-indol-3-yl)-, has demonstrated anti-fungal properties, making it a candidate for use in anti-fungal agents to combat fungal infections.

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 137-07-5 2-amino-benzenethiol 
• 57476-50-3 1-tert-butoxycarbonyl-3-formylindole 
• 88-73-3 2-Chloronitrobenzene 
• 120-72-9 indole 
• 95-16-9 1,3-Benzothiazole 
• 700-06-1 indole-3-carbinol 

Downstream Products

• 869585-26-2 3-(benzothiazol-2-yl)-1-(3,5-di-O-benzyl-β-D-ribofuranosyl)-1H-indole 
• 869585-20-6 3-(benzothiazol-2-yl)-1-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-1H-indole 
• 869585-14-8 3-(benzothiazol-2-yl)-1-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1H-indole 

Relevant academic research and scientific papers

Application of 2-substituted ethyl isothiocyanates and 2-aminothiols in the synthesis of the analogs of indole phytoalexin camalexin

Treatment of (indol-1-yl)magnesium bromide or iodide with 2-bromoethyl isothiocyanate afforded 1-(4,5-dihydrothiazol-2-yl)indole (6). Analogous reaction with 2,2-dimethoxyethyl isothiocyanate led to corresponding 1-thiocarbamoylindole derivative (7), which was cyclized to 1-(5-methoxy-4,5-dihydrothiazol-2-yl)indole (8) by treatment with boron trifluoride etherate. New analogs of camalexin, namely 4′,5′-dihydrocamalexin (12) and benzocamalexin (14) were prepared by cyclocondensation reaction of 1-(tert-butoxycarbonyl)indole-3-carbaldehyde with cysteamine and 2-aminobenzenethiol. Antifungal activity of the prepared compounds was studied, using the fungi Alternaria brassicae and Alternaria brassicicola.

Micellar catalysis enabled synthesis of indolylbenzothiazoles and their functionalization via Mn(II)-catalyzed C2–H amination using pyridones

The sustainable synthesis of indolylbenzothiazloes is reported utilising TPGS-750-M enabled nanomicellar catalysis in water. The reactions do not require additional catalysts and/or oxidants and proceed at room temperature. Subsequently, the indole rings were functionalized to construct novel tris-heterocyclic scaffolds via benzothiazole directed Mn(II)-catalyzed C2–H amination utilizing pyridones as the amine partner.

Camphor sulfonic acid catalyzed a simple, facile, and general method for the synthesis of 2-arylbenzothiazoles, 2-arylbenzimidazoles, and 3H-spiro[benzo[d]thiazole-2,3′-indolin]-2′-ones at room temperature

A simple, mild, eco-friendly, general, and convenient approach has been developed for the synthesis of structurally diverse 2-arylbenzothiazole derivatives from the reactions of 2-aminothiophenol and various aromatic aldehydes using camphor sulfonic acid

Ultrafine Pt nanoparticles supported on a dendrimer containing thiol groups: An efficient catalyst for the synthesis of benzimidazoles and benzothiazoles from benzyl alcohol derivatives in water

A novel and unique platform was prepared based on a dendrimer containing thiol groups supported on nanosilica (nSTDP), and ultrafine platinum nanoparticles were synthesized and immobilized on the thiol decorated branches of nSTPD. The new catalyst, (Ptnp?nSTDP), was characterized by different techniques such as FE-SEM, TEM, ICP, XPS and DR UV-vis. This heterogeneous catalyst presented an outstanding performance for the synthesis of benzimidazole and benzothiazole derivatives through a reaction between benzyl alcohol derivatives and 2-aminothiophenol or 1,2-phenylenediamine. No requirement for the pre-reduction of catalysts and using water as a green solvent make it an individual catalyst for these reactions. Furthermore, the catalyst can be easily recovered and reused five consecutive times in the production of benzimidazoles and benzothiazoles without significant leaching of Pt and loss of its activity which illustrated the chemical stability of the catalyst during the reaction.

Oxidative NHC catalysis for base-free synthesis of benzoxazinones and benzoazoles by thermal activated NHCs precursor ionic liquid catalyst using air as oxidant

A reusable thermal activated NHC precursor ionic liquid catalyst ([BMIm]2[WO4]) has been prepared and developed for the synthesis of nitrogen-containing heterocycles such as benzoxazinones and benzoazoles through imines activation. [BMIm]2[WO4] exhibited the good activity for the base-free condensation and oxidative NHC catalysis tandem under air atmosphere. The catalyst can be recovered and reused for at least five runs in gram scale synthesis without any decrease in catalytic activity. Furthermore, the control experiments demonstrated that the reaction involved formation of aromatic aldimines, NHC-catalyzed oxidative formation of imidoyl azoliums and intramolecular cyclization to generate the product.

Copper supported on functionalized MCM-41 as a novel and a powerful heterogeneous nanocatalyst for the synthesis of benzothiazoles

A new functionalized mesoporous catalyst (Cu(II)-Glycerol/MCM-41) has been synthesized as a highly efficient heterogeneous nanocatalyst for the synthesis of benzothiazoles derivatives. Powder XRD, TGA, TEM, SEM, EDX, BET, FT-IR and ICP-OES techniques are

Synthesis of Camalexin and Related Analogues

Camalexin is synthesized on a gram scale by coupling of thiazole and indole in an amidoalkylation–oxidation sequence. Several high-yielding implementations of this two-step approach are demonstrated with variation of either the intermediate acyliminium reagent or the oxidation conditions. Benzo-analogues and aza-analogues of the natural product are also obtained by this method. As a side result, a new formylation of indole is demonstrated.

Elemental sulfur as a polyvalent reagent in redox condensation with: O -chloronitrobenzenes and benzaldehydes: Three-component access to 2-arylbenzothiazoles

Sulfur was found to be a polyvalent reagent in the multicomponent redox condensation with o-chloronitrobenzenes and benzaldehydes. 2-Arylbenzothiazoles was obtained in moderate to good yields in a highly atom-economical pathway.

Visible-light-promoted synthesis of benzothiazoles from 2-aminothiophenols and aldehydes

A visible-light-promoted synthesis of benzothiazoles from 2-aminothiophenols and aldehydes has been developed. A wide range of aromatic, heteroaromatic and aliphatic aldehydes were successfully applied. The benzothiazole products were prepared in good yields. The reaction was carried out in the absence of transition-metal catalysts and extra additives. A radical reaction pathway was proposed.

Microwave assisted aqueous phase synthesis of benzothiazoles and benzimidazoles in the presence of Ag2O

A simple and high yielding method for synthesized benzothiazoles and benzimidazole in water under micro wave irradiation by the reaction of 2-amino thiophenol and o-phenylenediamine with various aromatic aldehydes in the presence of Ag2O. Agsu