883-93-2

Usage

Uses

Used in Environmental Monitoring:
2-Phenylbenzothiazole is used as a contaminant indicator in environmental studies, particularly for monitoring water and sediment quality in sedimentation ponds. Its detection in these environments helps assess the presence of pollutants and the effectiveness of wastewater treatment processes.
Used in Chemical Research:
2-Phenylbenzothiazole serves as a valuable compound in chemical research, where it can be utilized to study the properties and reactions of benzothiazoles and their derivatives. This knowledge can contribute to the development of new materials, pharmaceuticals, and other applications.
Used in Industrial Applications:
Although not explicitly mentioned in the provided materials, 2-Phenylbenzothiazole may also have potential uses in various industrial applications, such as in the synthesis of dyes, pigments, or as intermediates in the production of other organic compounds. Its specific role in these industries would depend on the requirements and properties needed for the end product.

InChI:InChI=1/C13H9NS/c1-2-6-10(7-3-1)13-14-11-8-4-5-9-12(11)15-13/h1-9H

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 98-88-4 benzoyl chloride 
• 98-87-3 benzylidene dichloride 
• 98370-54-8 zinc 2-aminobenzenethiolate 
• 93-98-1 N-phenyl benzoyl amide 
• 51942-32-6 2-(benzoylamino)-1-(methylthio)benzene 
• 67-56-1 methanol 
• 31230-83-8 2-Phenylbenzothiazolin 
• 74-88-4 methyl iodide 
• 758640-21-0 N-Benzylaniline 
• 17435-12-0 N,N-Diphenylthiobenzamid 
• 614-30-2 N-methyl-N-phenyl-benzenemethanamine 
• 1047-61-6 1-thiobenzoyloxy-2-(N-benzoylamino)benzene 
• 85433-21-2 N-(2-bromophenyl)benzothioamide 

Downstream Products

• 2783-66-6 1-methyl-2-phenylbenzothiazolium iodide 
• 77333-67-6 6-bromo-2-phenylbenzo[d]thiazole 
• 38338-23-7 6-nitro-2-phenyl-benzothiazole 
• 137-07-5 2-amino-benzenethiol 
• 65-85-0 benzoic acid 
• 67362-98-5 2-([1,1′-biphenyl]-4-yl)benzo[d]thiazole 
• 91258-40-1 C₄₂H₄₈N₂S₂ 
• 79091-78-4 3-ethoxy-4-phenyl-2,3-dihydro-1,5-benzothiazepine 
• 83463-85-8 4-ethoxy-3-methyl-2-phenylquinoline 
• 83463-84-7 3-ethoxy-4-methyl-2-phenylquinoline 
• 83463-81-4 3-ethoxy-2-methyl-4-phenyl-1,5-benzothiazepine 
• 83463-82-5 2-ethoxy-3-methyl-4-phenyl-1,5-benzothiazepine 
• 83463-83-6 4-ethoxy-3-methyl-2-phenyl-1,5-benzothiazepine 
• 83463-80-3 3-ethoxy-2-phenylquinoline 

Relevant academic research and scientific papers

Synthesis of 2-Arylbenzothiazoles from Nitrobenzenes, Benzylamines, and Elemental Sulfur via Redox Cyclization

A sustainable advanced synthetic method was developed based on redox cyclization for the synthesis of 2-arylbenzothiazoles in good to excellent yields from readily available nitrobenzenes, benzylamines, and elemental sulfur without the use of transition-metal catalysts. This method is remarkable: nitro group reduction, a benzylamine redox reaction, sulfuration, condensation, and cyclization, all proceed in a single step to generate a heterocycle. It is also highly atom-economical and does not require any external oxidizing or reducing agents.

Graphene oxide-catalyzed synthesis of benzothiazoles with amines and elemental sulfur via oxidative coupling strategy of amines to imines

The graphene oxide-catalyzed coupling and cyclization reactions of primary amines with elemental sulfur was developed to afford various optically property benzothiazoles. This coupling and cyclization strategies proceeded under the oxidant system graphene oxide/O2 and constructed carbon-heteroatom (N, S) bonds with amines and elemental sulfur. Due to benzothiazoles as common chromophores, these products exhibited intriguing fluorescence properties, including outstanding Stokes shifts (up to 161 nm) and quantum yields (up to 74%). Utilizing the products’ unique fluorescence response in different solvents, β-naphthothiazole 4a showed excellent aggregation-induced emission properties in 1,2-dichloroethane, which was 60 times higher than in tetrahydrofuran.

UV-visible light-induced photochemical synthesis of benzimidazoles by coomassie brilliant blue coated on W-ZnO@NH2nanoparticles

Heterogeneous photocatalysts proffer a promising method to actualize eco-friendly and green organic transformations. Herein, a new photochemical-based methodology is disclosed in the preparation of a wide range of benzimidazoles through condensation of o-phenylenediamine with benzyl alcohols in the air under the illumination of an HP mercury lamp in the absence of any oxidizing species catalyzed by a new photocatalyst W-ZnO@NH2-CBB. In this photocatalyst, coomassie brilliant blue (CBB) is heterogenized onto W-ZnO@NH2 to improve the surface characteristics at the molecular level and enhance the photocatalytic activity of both W-ZnO@NH2 and CBB fragments. This unprecedented heterogeneous nanocatalyst is also identified by means of XRD, FT-IR, EDS, TGA-DTG, and SEM. The impact of some influencing parameters on the synthesis route and effects on the catalytic efficacy of W-ZnO@NH2-CBB are also assessed. The appropriate products are attained for both the electron-withdrawing and electron-donating substituents in the utilized aromatic alcohols. Furthermore, preparation of benzimidazoles is demonstrated to occur mainly via a radical mechanism, which shows that reactive species such as ·O2-, OH and h+ would be involved in the photocatalytic process. Stability and reusability studies also warrant good reproducibility of the nanophotocatalyst for at least five runs. Eventually, a hot filtration test proved that the nanohybrid photocatalyst is stable in the reaction medium. Using an inexpensive catalyst, UV-vis light energy and air, as a low cost and plentiful oxidant, puts this methodology in the green chemistry domain and energy-saving organic synthesis strategies. Finally, the anticancer activity of W-ZnO nanoparticles is investigated on MCF7 breast cancer cells by MTT assay. This experiment reveals that the mentioned nanoparticles have significant cytotoxicity towards the selected cell line.

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.

Nickel catalyzed sustainable synthesis of benzazoles and purines: Via acceptorless dehydrogenative coupling and borrowing hydrogen approach

Herein we report nickel-catalyzed sustainable synthesis of a few chosen five-membered fused nitrogen heterocycles such as benzimidazole, purine, benzothiazole, and benzoxazole via acceptorless dehydrogenative functionalization of alcohols. Using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst, [Ni(MeTAA)] (1a), featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)), a wide variety of polysubstituted benzimidazole, purine, benzothiazole, and benzoxazole derivatives were prepared via dehydrogenative coupling of alcohols with 1,2-diaminobenzene, 4,5-diaminopyrimidine, 2-aminothiphenol, and 2-aminophenol, respectively. A wide array of benzimidazoles were also prepared via a borrowing hydrogen approach involving alcohols as hydrogen donors and 2-nitroanilines as hydrogen acceptors. A few control experiments were performed to understand the reaction mechanism.

Photocatalytic green synthesis of benzazoles from alcohol oxidation/toluene sp3C-H activation over metal-free BCN: effect of crystallinity and N-B pair exposure

Porous borocarbonitride (P-BCN), with the characteristics of enhanced crystallinity and improved N-B pair exposure, was prepared with a simple KCl-assisted molten salt strategy. Efficient heterogeneous photocatalytic tandem synthesis of benzazoles from alcohol oxidation/toluene sp3C-H activation was achieved firstly over the metal-free P-BCN using visible light and the green oxidant O2, with only water as a by-product. Variouso-thio/hydroxy/aminoanilines and alcohols or toluenes could be converted to the corresponding 2-substituted benzothiazoles, benzoxazoles and benzimidazoles with good to excellent photocatalytic performance. The improved photocatalytic performance in comparison to bulk BCN should be due to the crystallinity-enhancement-induced improvement in charge separation and transmission. The increased N-B pair exposure promoted superoxide radical generation due to the electron-enriched N atoms, as well as improved oxidation ability due to the valence band constructed by the B 2p orbital. This work presents a green and efficient synthetic strategy towards benzazoles and other fine chemicalsviametal-free heterogeneous photocatalysis.

Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen

The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.

Highly Ordered Mesoporous Cobalt Oxide as Heterogeneous Catalyst for Aerobic Oxidative Aromatization of N-Heterocycles

N-heterocycles are key structures for many pharmaceutical intermediates. The synthesis of such units normally is conducted under homogeneous catalytic conditions. Among all methods, aerobic oxidative aromatization is one of the most effective. However, in homogeneous conditions, catalysts are difficult to be recycled. Herein, we report a heterogeneous catalytic strategy with a mesoporous cobalt oxide as catalyst. The developed protocol shows a broad applicability for the synthesis of N-heterocycles (32 examples, up to 99 % yield), and the catalyst presents high turnover numbers (7.41) in the absence of any additives. Such a heterogenous approach can be easily scaled up. Furthermore, the catalyst can be recycled by simply filtration and be reused for at least six times without obvious deactivation. Comparative studies reveal that the high surface area of mesoporous cobalt oxide plays an important role on the catalytic reactivity. The outstanding recycling capacity makes the catalyst industrially practical and sustainable for the synthesis of diverse N-heterocycles.

Orderly cascade of immobilized-enzyme catalysis and photocatalysis for continuous-microflow production of 2-phenylbenzothiazole

Green, economic, efficient, and sustainable synthesis of 2-phenylbenzothiazole (2-PBZ)—an important versatile scaffold—remains challenging. Here, for the first time, we propose to cascade immobilized enzyme catalysis and photocatalysis in a continuous-microflow manner to realize the online reuse of the enzyme, eliminate cross-inhibitions between the two-step reaction processes, provide stronger and more uniform illumination, and enhance process efficiency. This novel microflow system required only 4.6 min of the total residence time to achieve >99% product yield, and 93.7% of the total catalytic activity was retained after running for 300 min. This orderly cascaded continuous-flow microreactor system widens the limitations of photo-biocatalytic approaches and provides the potential foundation for the industrial green production of 2-PBZ.

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.