38338-23-7

Usage

Uses

Used in Biotechnology:
6-NITRO-2-PHENYLBENZOTHIAZOLE is used as a fluorescent probe for measuring pH in biological systems, providing valuable insights into cellular processes and environmental conditions within living organisms.
Used in Pharmaceutical Industry:
6-NITRO-2-PHENYLBENZOTHIAZOLE is used as an antitumor agent due to its potential to inhibit tumor growth and progression. Its application in medicinal chemistry is further supported by its photophysical properties, which may contribute to the development of novel therapeutic agents.
Used in Materials Science:
6-NITRO-2-PHENYLBENZOTHIAZOLE is used in the development of optical and imaging applications, leveraging its photophysical properties to enhance the performance of various materials and devices in this field.

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

Upstream product

• 883-93-2 2-Phenylbenzothiazole 
• 538-51-2 benzylidene phenylamine 
• 5265-19-0 N-(4-nitrophenyl)thiobenzamide 
• 98-88-4 benzoyl chloride 
• 100-01-6 4-nitro-aniline 
• 2942-06-5 6-nitrobenzo[d]thiazole 
• 23451-98-1 2-amino-5-nitrobenzenethiol 
• 65-85-0 benzoic acid 
• 95-16-9 1,3-Benzothiazole 
• 6293-83-0 2-iodo-4-nitrophenylamine 
• 108-88-3 toluene 
• 108-86-1 bromobenzene 
• 100-46-9 benzylamine 
• 98-91-9 thiobenzoic acid 

Downstream Products

• 6392-97-8 2-phenylbenzo[d]thiazole-6-amine 
• 1426262-55-6 C₂₈H₃₄N₄OS₂ 
• 1426262-52-3 C₂₈H₃₂N₄O₂S₂ 
• 1426262-48-7 C₁₅H₁₁ClN₂OS 

Relevant academic research and scientific papers

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.

Design, synthesis and biological evaluation of new benzoxazolone/benzothiazolone derivatives as multi-target agents against Alzheimer's disease

In this study, four series of compounds with benzoxazolone and benzothiazolone cores were designed, synthesized and evaluated as multifunctional agents against Alzheimer's disease (AD). Additionally, in order to shed light on the effect of the carbonyl groups of benzoxazolone/benzothiazolone, benzoxazole/benzothiazole-containing analogues were also synthesized and evaluated. Inhibition potency of all final compounds towards cholinesterase enzymes and their antioxidant activity were tested. Subsequently, the anti-inflammatory activity, cytotoxicity, apoptosis, and Aβ aggregation inhibition tests were also performed for selected compounds. The results indicated that compounds 11c, a pentanamide derivative with benzothiazolone core, and 14b, a keton derivative with benzothiazolone core, were considered as promising multi-functional agents for further investigation against AD. The reversibility, kinetic and molecular docking studies were also performed for the compounds with the highest AChE 14b (eeAChE IC50 = 0.34 μM, huAChE IC50 = 0.46 μM) and BChE 11c (eqBChE IC50 = 2.98 μM, huBChE IC50 = 2.56 μM) inhibitory activities.

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.

Riboflavin as Photoredox Catalyst in the Cyclization of Thiobenzanilides: Synthesis of 2-Substituted Benzothiazoles

Benzothiazoles are synthesized from thiobenzanilides using riboflavin as a photosensitizer and potassium peroxydisulfate as a sacrificial oxidizing agent under visible light irradiation. The methodology accepts a broad range of functional groups and affords the 2-substituted benzothiazoles by transition-metal-free organic photoredox catalysis under very mild conditions.

Copper-Catalyzed Benzylic C—H Functionalization, Oxidation and Cyclization of Methylarenes: Direct Access to 2-Arylbenzothiazoles

The direct C—H functionalization of methylarenes is of great significance. Herein, a copper-catalyzed oxidative C—N/C—S bond formation through benzylic C(sp3)—H functionalization, oxidation and cyclization of methylarenes is reported. Various 2-arylbenzothiazoles have been synthesized in moderate to excellent yields with readily available o-iodoaniline, potassium sulfide, and methylarenes as raw materials.

Method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions

The invention discloses a method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions. According to the method, glacial aceticacid is taken as a catalyst; at solvent-free room temperature conditions, physical grinding is adopted, reaction of 2-substituted arylamines (2-mercapto arylamine, 2-aminophenol, and o-phenylenediamine) and aromatic aldehydes is carried out using physical grinding. The method is friendly to the environment, is simple in operation, is safe, is low in cost, and is high in efficiency. Compared withthe prior art, the advantages are that: the method is suitable for a large amount of functional groups, yield is high, less by-product is generated, operation is simple, the method is safe, cost is low, and the method is friendly to the environment.

A medicine intermediate 2 - aryl benzo thiazole synthetic method of compound (by machine translation)

The invention relates to a kind of the following formula (III) is shown in the 2 - aryl benzo thiazole compound synthesis method, The method includes: in the three-component composite in the solvent, the catalyst, in the presence of alkali and accelerator, the following formula (I) compound with the following formula (II) compound to react, thus get the states the type (III) compound, Wherein R1 , R2 Are each independently selected from H, C1 - C6 Alkyl, C1 - C6 Alkoxy, halogen or nitro; X is halogen. The method through the catalyst, alkali, accelerator and three-component solvent system selected, combined, so as to play a unique synergy, achieved excellent product yield, has industrial application in the medical field of the actual value. (by machine translation)

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.

Direct arylation of benzoazoles with aldehydes utilizing metal-organic framework Fe3O(BDC)3 as a recyclable heterogeneous catalyst

A metal-organic framework Fe3O(BDC)3 was synthesized and used as a recyclable heterogeneous catalyst for the direct arylation of azoles with benzaldehydes. Following this protocol, inexpensive and commercially available benzaldehydes could act as an aryl source for the transformation, replacing the aryl halides normally employed in the conventional cross-coupling reactions. The catalyst disclosed higher catalytic productivity for the formation of aryl-substituted azoles than various MOFs and diverse homogeneous iron catalysts. The conversion was considerably regulated by the solvent and the oxidant, and the combination of N-methyl-2-pyrrolidone with di-tert-butyl peroxide offered the best yield. Heterogeneous catalysis was verified for the reaction, and the production of aryl-substituted azoles was only feasible in the presence of the iron framework. It was possible to reuse the catalyst for the direct arylation of azoles with aldehydes while its catalytic activity was preserved for multiple cycles. To our best judgment, this direct arylation of azoles with aldehydes utilizing solid catalysts has not been previously reported.