6269-45-0

Usage

Molecular Weight

240.28 g/mol

Physical Appearance

Yellow crystalline powder

Common Uses

+ Manufacturing of fluorescent dyes and optical brighteners
+ Potential applications in organic electronic devices
+ Photosensitizer in photodynamic therapy

Biological Properties

+ Antimicrobial properties
+ Anticancer properties

Safety Precautions

+ Harmful if ingested, inhaled, or in contact with the skin
+ May cause eye and skin irritation
+ Handle with caution

InChI:InChI=1/C13H8N2O2S/c16-15(17)11-7-3-1-5-9(11)13-14-10-6-2-4-8-12(10)18-13/h1-8H

Upstream product

• 137-07-5 2-amino-benzenethiol 
• 552-89-6 2-nitro-benzaldehyde 
• 610-14-0 2-nitrobenzyl chloride 
• 552-16-9 ortho-nitrobenzoic acid 
• 95-16-9 1,3-Benzothiazole 
• 25373-33-5 2-(2-nitrophenyl)-2,3-dihydrobenzothiazole 
• 25364-36-7 C₁₃H₁₀N₂O₂S 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 80379-10-8 1-(2-nitrophenyl)ethan-1-ol 
• 612-25-9 2-Nitrobenzyl alcohol 
• 577-59-3 2-acetylnitrobenzene 
• 1969-73-9 (2-nitrophenyl)acetaldehyde 
• 15121-84-3 2-nitro-benzeneethanol 
• 17408-15-0 1-(2-nitrophenyl)propanone 

Downstream Products

• 29483-73-6 2-(2-aminophenyl)benzthiazole 
• 60418-20-4 indazolo<3,2-b>benzothiazole 
• 60418-15-7 2-(2-Azidophenyl)benzothiazole 
• 162374-54-1 2-(2-Amino-5-trifluoromethylsulfonyloxyphenyl)benzothiazole 
• 174536-61-9 Trifluoro-methanesulfonic acid 3-benzothiazol-2-yl-4-(2,2,2-trifluoro-acetylamino)-phenyl ester 
• 3682-71-1 2-phenyl-2H-indazole 
• 32286-81-0 2-phenyl-4,5,6,7-tetrahydro-2H-indazole 
• 1092936-34-9 2-[2-(t-Boc-L-alanylamino)phenyl]benzothiazole 
• 1310352-08-9 2-[2-(t-Boc-β-alanylamino)phenyl]benzothiazole 
• 111195-94-9 N-(2-(benzo[d]thiazol-2-yl)phenyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Ultrasound-assisted efficient and green synthesis of 2-substituted benzothiazoles under solvent-free condition using recyclable sulfated tungstate

Sulfated tungstate catalyzed an efficient and ecofriendly protocol has been described for the synthesis of 2-substituted benzothiazoles. The corresponding benzothiazoles were obtained using a condensation reaction of 2-aminothiophenol with various aldehydes under ultrasound irradiation at room temperature. Various functional groups on the 2-aminothiophenol as well as on the aldehydes were tolerated to provide 2-substituted benzothiazoles derivatives in excellent yields. The faster reaction rate, solvent-free or mild reaction conditions, wide functional group compatibility, excellent yields, easy work-up procedure, and excellent catalyst recyclability are the advantages of this protocol. These advantages make this process more practicable, cost-effective, and environmentally benign.

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

Pentafluorophenylammonium Triflate: A Mild, Efficient and Reusable Catalyst for the Synthesis of 2-Arylbenzothiazole and 2-Arylbenzothiazoline Derivatives in a Green Chemical Approach

In this work, one pot, simple and environmentally benign effective synthesis of 2-substituted benzothiazole and benzothiazoline derivatives are described in presence of PFPAT (pentafluorophenylammonium triflate) catalyst in water successfully. A series of benzothiazole derivative were synthesized by the reaction between 2-aminothiophenol and various aldehydes in good yields. Recyclability of the catalyst is observed for four times without loss of its activity in aqueous medium.

ZnO-NPs catalyzed condensation of 2-aminothiophenol and aryl/alkyl nitriles: Efficient green synthesis of 2-substituted benzothiazoles

The synthesis of 2-substituted benzothiazoles has been described using ZnO-nanoparticles as a catalyst. The condensation of 2-aminothiophenol and aryl/alkyl nitriles resulted in the formation of various 2-substituted benzothiazoles under solvent-free reaction conditions. The library of 2-substituted benzothiazoles has been synthesized in good to excellent yield. The reaction has shown a wide range of functional group compatibility for both varyingly substituted 2-aminothiophenols and nitriles. The protocol has many advantages such as faster reaction rate, mild reaction conditions, various functional group compatibility, excellent yield, solvent-free reaction conditions, easy recovery of materials, and excellent catalyst recyclability, among others. The various advantages of this protocol make it a more feasible, economical, and environmentally benign process.

Synthesis of thioethers, arenes and arylated benzoxazoles by transformation of the C(aryl)-C bond of aryl alcohols

Transformation of aryl alcohols into high-value functionalized aromatic compounds by selective cleavage and functionalization of the C(aryl)-C(OH) bond is of crucial importance, but very challenging by far. Herein, for the first time, we report a novel and versatile strategy for activation and functionalization of C(aryl)-C(OH) bonds by the cooperation of oxygenation and decarboxylative functionalization. A diverse range of aryl alcohol substrates were employed as arylation reagents via the cleavage of C(aryl)-C(OH) bonds and effectively converted into corresponding thioether, arene, and arylated benzoxazole products in excellent yields, in a Cu based catalytic system using O2 as the oxidant. This study offers a new way for aryl alcohol conversion and potentially offers a new opportunity to produce high-value functionalized aromatics from renewable feedstocks such as lignin which features abundant C(aryl)-C(OH) bonds in its linkages.

NCS/TBHP promoted C2 arylation of benzothiazoles with aldehydes in DMSO

A N-chlorosuccinimide catalyzed oxidative synthesis of 2-aryl benzothiazole from benzothiazoles and aryl aldehydes using tert-butyl peroxybenzoate as an oxidant in dimethyl sulfoxide (DMSO) has been developed in moderate to good yields. Solvent DMSO as a strong Lewis base plays an efficient role in the reaction. Various substrates were tolerated under optimized conditions affording the arylated products in 12–94% yields for 28 examples. Additionally, acylated benzothiazoles were produced with 4 examples.

Preparation method of substituted benzothiazole C2 arylated derivative

The invention discloses a substituted benzothiazole C2 arylated derivative and a preparation method thereof. The preparation method comprises the following steps: mixing substituted benzothiazole represented by a formula (II) and substituted benzaldehyde represented by a formula (III); adding a free radical initiator N-chlorosuccinimide (NCS) and an oxidant tert-butyl hydroperoxide (TBHP), carrying out a stirring reaction for about 12 h at 120 DEG C in a nitrogen atmosphere by using DMSO as a solvent, and after the reaction is finished, separating and purifying the reaction liquid to prepare the substituted benzothiazole C2 arylated derivative represented by a formula (I). The invention provides a new method for synthesizing a benzothiazole C2 arylated derivative by taking an NCS/TBHP double component as an oxidation system through a stirring and reaction for about 12 hours at 120 DEG C in a nitrogen atmosphere under the assistance of a strong Lewis base DMSO; and according to the method, an NCS/TBHP double-component oxidation system and an aprotic solvent are selected, and the method has the advantages of being simple in catalytic system, good in product yield and wide in substrate range.

Synthesis and characterization of a new poly(N–heterocyclic carbene Cu complex) immobilized on nano–silica, (CuII–NHCs)n@nSiO2, and its application as an efficient and reusable catalyst in the synthesis of benzimidazoles,

The present study describes the synthesis and characterization of a new poly(N–heterocyclic carbene Cu complex) immobilized on nano silica, (CuII–NHCs)n@nSiO2. The (CuII–NHCs)n@nSiO2 dendri

Method for synthesizing benzothiazole by microwave radiation of benzothioamide compound in aqueous phase

The invention discloses a method for synthesizing benzothiazole by microwave radiation of a benzothioamide compound in an aqueous phase. The method includes the steps: adding the benzothioamide compound into the aqueous phase under microwave conditions; performing cyclization under alkaline conditions to generate the benzothiazole. The method for preparing the benzothiazole is environmentally friendly, simple and convenient in operation, safe, cheap and efficient. Compared with the prior art, the method is applicable to a lot of functional groups, high in yield, few in by-products, simple in operation, safe, low in cost and environmentally friendly.

Method for preparing benzothiazole compound through microwave catalysis in water phase

The invention discloses a method for preparing a benzothiazole compound through/under microwave catalysis in a water phase. A water-soluble coordination compound is used as a catalyst, and a reactionof inorganic sulfide, 2-iodoaniline and aldehyde is efficiently catalyzed through microwaves in a pure water phase. The method for preparing the benzothiazole compound is environmentally friendly, convenient to operate, safe, cheap and efficient. Compared with the prior art, the method is applied to a large quantity of functional groups, high in yield, simple to operate, safe, low in cost and environmentally friendly and produces a few byproducts.