15903-58-9

Usage

Uses

Used in Textile Industry:
2-(O-TOLYL)BENZOTHIAZOLE is used as a fluorescent brightener to enhance the appearance of textiles, providing them with a brighter and more vibrant look.
Used in Plastics Industry:
In the plastics industry, 2-(O-TOLYL)BENZOTHIAZOLE serves as a fluorescent brightener, improving the visual appeal of plastic products by making them appear more luminous and attractive.
Used as an Intermediate in Organic Synthesis:
2-(O-TOLYL)BENZOTHIAZOLE is utilized as an intermediate in the synthesis of other organic compounds, contributing to the development of new chemical products and materials.

InChI:InChI=1/C14H11NS/c1-10-6-2-3-7-11(10)14-15-12-8-4-5-9-13(12)16-14/h2-9H,1H3

Upstream product

• 529-20-4 2-methylphenyl aldehyde 
• 137-07-5 2-amino-benzenethiol 
• 95-16-9 1,3-Benzothiazole 
• 95-49-8 2-methylchlorobenzene 
• 95-46-5 2-methylphenyl bromide 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 89-92-9 2-methylbenzyl bromide 
• 615-43-0 2-iodophenylamine 
• 933-88-0 ortho-toluoyl chloride 
• 305858-45-1 N-(2-iodophenyl)-2-methylbenzamide 
• 89-95-2 2-methyl-benzyl alcohol 
• 136-95-8 2-amino-benzthiazole 
• 1039834-46-2 2-iodo-N-(2-methylbenzyl)aniline 
• 89-93-0 ortho-methylbenzylamine 

Downstream Products

• 212520-27-9 Cu(C₈H₇O₂)2(C₇H₄NSC₆H₄CH₃)2 
• 590369-34-9 di(thiocyanato-N)tetrakis(2-(2'-tolyl)-benzothiazole)nickel(II) 
• 1440999-99-4 2-(benzo[d]thiazol-2-yl)-3-methylphenyl pivalate 
• 1440999-76-7 2-(benzo[d]thiazol-2-yl)-3-methylphenyl acetate 
• 1242299-59-7 C₁₄H₁₀BrNS 
• 1454287-64-9 (2-(benzo[d]thiazol-2-yl)-3-methylphenyl)(phenyl)methanone 

Relevant academic research and scientific papers

Reversible conversion of valence-tautomeric copper metal-organic frameworks dependent single-crystal-to-single-crystal oxidation/reduction: A redox-switchable catalyst for C-H bonds activation reaction

Upon single-crystal-to-single-crystal (SCSC) oxidation/reduction, reversible structural transformations take place between the anionic porous zeolite-like CuI framework and a topologically equivalent neutral CuICuII mixed-valent framework. The unique conversion behavior of the CuI framework endowed it as a redox-switchable catalyst for the direct arylation of heterocycle C-H bonds.

Fast and high-efficiency synthesis of 2-substituted benzothiazoles via combining enzyme catalysis and photoredox catalysis in one-pot

An efficient and green method, combining enzymatic and visible-light catalysis for synthesis of the widely applicable 2-substituted benzothiazoles, has been developed. This method features a relay catalysis protocol consisting of biocatalytic promiscuity

Synthesis of benzothiazoles using fluorescein as an efficient photocatalyst under visible light

This work reports a novel and efficient method for the synthesis of benzothiazoles using 2-aminothiophenol derivatives in conjunction with aromatic aldehyde as starting materials via visible-light-induced condensation cyclization. Utilizing fluorescein as the photocatalyst and blue LED lamp as the light source, the reaction proceeds in the presence of a molecular oxygen atmosphere without the need for metal catalyst or an additional oxidant. Significantly, this method exhibits good tolerance in substrates, and a variety of 2-aminothiophenol derivatives and aromatic aldehyde are amenable to producing the corresponding benzothiazoles in high to excellent yields.

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.

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.

Mechanochemical Solvent-Free Catalytic C?H Methylation

The mechanochemical, solvent-free, highly regioselective, rhodium-catalyzed C?H methylation of (hetero)arenes is reported. The reaction shows excellent functional-group compatibility and is demonstrated to work for the late-stage C?H methylation of biologically active compounds. The method requires no external heating and benefits from considerably shorter reaction times than previous solution-based C?H methylation protocols. Additionally, the mechanochemical approach is shown to enable the efficient synthesis of organometallic complexes that are difficult to generate conventionally.

Improved, gram-scale synthesis of sildenafil in water using arylacetic acid as the acyl source in the pyrazolo[4,3-d]pyrimidin-7-one ring formation

An improved, gram-scale synthesis of the blockbuster drug sildenafil, used for the treatment of male erectile dysfunction, has been developed. Unlike the previous literature, the current method demonstrates the use of arylacetic acid as an acyl source, a cheap oxidant K2S2O8, and water as the reaction medium in the key step of pyrrazolo[4,3-d]pyrimidin-7-one ring formation. As well as being a green and benign approach, the current method reduces the cost by half compared to our previous strategy. In addition, the general relevance of the method has been demonstrated in the synthesis of a variety of quinazolinone and benzothiazole derivatives with excellent functional group tolerance.

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.

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).

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.