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 
• 6270-76-4 2-methyl-2-phenyl-2,3-dihydrobenzo[d]thiazole 
• 85433-21-2 N-(2-bromophenyl)benzothioamide 
• 538-51-2 benzylidene phenylamine 
• 56-23-5 tetrachloromethane 
• 100-52-7 benzaldehyde 
• 137-07-5 2-amino-benzenethiol 
• 1141-88-4 2-Aminophenyl disulfide 
• 103-72-0 phenyl isothiocyanate 
• 64-19-7 acetic acid 

Downstream Products

• 67362-98-5 2-([1,1′-biphenyl]-4-yl)benzo[d]thiazole 
• 53544-74-4 2-(4'-nitrophenyl)-6-nitrobenzothiazole 
• 90481-43-9 2-(2,3-dihydroxyphenyl)-1,3-benzothiazole 
• 112590-97-3 C₆H₄SNCC₆H₅BH₃ 
• 52797-55-4 N-(2-phenylmethyl)2-mercaptoaniline 
• 152993-87-8 2-(2,6-difluorophenyl)-1,3-benzothiazole 
• 1747-46-2 2-(2-fluorophenyl)-1,3-benzothiazole 
• 1454287-80-9 (2-(benzo[d]thiazol-2-yl)-4-methylphenyl)(phenyl)methanone 

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.

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.

KOtBu-Promoted Halogen-Bond-Assisted Intramolecular C-S Cross-Coupling of o-Iodothioanilides for the Synthesis of 2-Substituted Benzothiazoles

An efficacious and mild KOtBu-promoted intramolecular C-S cross-coupling of ortho-iodothioanilides in conjunction with a catalytic quantity of phenanthroline as an additive has been described for the convenient synthesis of 2-substituted benzothiazoles. The methodology is suitable for attaining a wide variety of 2-alkyl- and 2-aryl-substituted benzothiazoles. Single-crystal XRD, DFT calculations, NMR, and UV studies suggest that halogen bonds between the units of ortho-iodothioanilides may assist in the electron transfer process.

Preparation method of benzothiazole phosphate compound

The invention discloses a preparation method of a benzothiazole phosphate compound. Under the irradiation of visible light, N-(2-bromophenyl) alkyl thioamide such as N-(2-bromophenyl) alkyl thioamide derivatives and the like are used as raw materials, sodium phosphate is used as alkali, a series of 2-substituted alkyl benzothiazole derivatives are smoothly synthesized, and further, under the irradiation of visible light, the benzothiazole phosphate compound is prepared through reaction with diethyl phosphate, and the benzothiazole phosphate compound has the calcium antagonist capability.

Method for preparing biphenyl benzothiazole compound

The invention discloses a preparation method of a biphenyl benzothiazole compound. N-(2-bromophenyl) alkyl thioamide such as an N-(2-bromophenyl) alkyl thioamide derivative is used as a raw material, sodium phosphate is used as alkali, the biphenyl benzothiazole compound is prepared through a one-pot method, the reaction is carried out under visible light irradiation, metal ions disclosed in the prior art are not needed, and the reaction yield is high.

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).

Possible competitive modes of decarboxylation in the annulation reactions ofortho-substituted anilines and arylglyoxylates

Annulation reactions ofortho-substituted anilines and arylglyoxylates in the presence of K2S2O8at 80 °C under metal-free neutral conditions have been investigated, which extended a platform for the tandem synthesis of nitrogen heterocycles. While arylglyoxylic acids are known to undergo decarboxylation to form an acyl radical in the presence of K2S2O8and used in the Minisci acylation of electron-deficient (hetero)aromatics, their reactions with electron-richortho-substituted anilines to form nitrogen heterocycles have recently been studied. Depending upon the experimental conditions used in the reactions, the mechanism of the formation of heterocycles involving reactions of an acyl radical or aryl iminocarboxylic acids has been postulated. Given the subtle understanding of the mechanisms of annulation reactions of 2-substituted anilines and arylglyoxylates in the presence of K2S2O8, an extensive mechanistic investigation was undertaken. In the current study, the various mechanistic pathways including the generation of acyl, imidoyl, aminal, and N,O-hemiketal radicals have been postulated based on different possible decarboxylation modes. Some of the proposed intermediates are supported based on the available analytical data. The protocol uses a single, inexpensive reagent K2S2O8, which offers not only transition-metal-free conditions but also serves as the reagent for the key decarboxylation step. Taken together, this study complements the current development of the annulation reactions of 2-substituted anilines and arylglyoxylates in terms of synthesis and mechanistic understanding.

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water

Herein, a borax–mediated convenient and efficient strategy for the synthesis of prominent structurally diverse N, S-heterocycles such as quinazolin-4(3H)-one, benzothiadiazine 1,1-dioxide, benzothioazole, and benzoxazoles from readily available 2-aminobenzamide/2-aminobenzenesulfonamide/2-aminothiophenol/2-aminophenol with α,α,α-trihalotoluenes at 100 ℃ in water is elaborated. Upon using aldehydes instead of α,α,α-trihalotoluenes, the reactions proceed through domino fashion under the catalytic effect borax to yield 2,3-dihydroquinazolin-4(1H)-one, 3,4-dihydrothiadiazine 1,1-dioxide, and benzothiazoles in one-pot at 60 ℃. The advantages of this protocol are practical simplicity, large substrate scope, moderate to excellent yields, and the use of water as the solvent.