10002-44-5

Basic information

• Product Name: 2-(2-Methoxy-phenyl)-benzothiazole
• Synonyms: Benzothiazole,2-(m-methoxyphenyl)- (7CI); 2-(3-Methoxyphenyl)benzo[d]thiazole;2-(3-Methoxyphenyl)benzothiazole; 2-(3'-Methoxyphenyl)benzothiazole
• CAS NO: 10002-44-5
• Molecular Formula: C₁₄H₁₁NOS
• Molecular Weight: 0
• Mol File: 10002-44-5.mol
• Article Data: 78

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2-Methoxy-phenyl)-benzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Methoxy-phenyl)-benzothiazole(10002-44-5)
• EPA Substance Registry System: 2-(2-Methoxy-phenyl)-benzothiazole(10002-44-5)

Safety Data

• Hazardous Substances Data: 10002-44-5(Hazardous Substances Data)

Usage

Appearance

Yellow solid The compound's physical form and color, which is a yellow-colored solid substance.

Molecular weight

253.32 g/mol The mass of one mole of the compound, which is 253.32 grams.

Usage as a fluorescent probe

Detection of metal ions, particularly copper The compound's application in detecting the presence of metal ions, especially copper ions, through its fluorescent properties.

Potential antiproliferative activity

Inhibition of cell proliferation The compound's ability to potentially prevent the rapid increase in the number of cells, which can be useful in treating diseases like cancer.

Potential antitumor activity

Suppression of tumor growth The compound's capability to hinder the development and expansion of tumors, making it a possible candidate for cancer treatment.

Upstream product

• 136-95-8 2-amino-benzthiazole 
• 6971-51-3 3-methoxybenzyl alcohol 
• 137-07-5 2-amino-benzenethiol 
• 95-16-9 1,3-Benzothiazole 
• 626-20-0 3-methoxystyrene 
• 5071-96-5 3-METHOXYBENZYLAMINE 
• 1612227-90-3 N-(2-iodophenyl)-3-methoxybenzothioamide 
• 586-38-9 3-Methoxybenzoic acid 
• 331989-36-7 C₁₄H₁₂BrNO₂ 
• 1711-05-3 m-anisoyl chloride 
• 615-36-1 2-bromoaniline 
• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 62-53-3 aniline 
• 1527-89-5 3-methoxybenzonitrile 

Downstream Products

• 25389-28-0 3-benzothiazol-2-yl-phenol 
• 1305316-85-1 O-[3-(1,3-benzothiazol-2-yl)phenyl]diphenylthiophosphinate 

Relevant articles and documents

Rapid and convenient thermal or microwave-assisted synthesis of substituted 2-phenylbenzothiazoles

A simple one-step method for the synthesis of biologically relevant 2-phenylbenzothiazoles has been developed, using sodium metabisulfite as an oxidant following condensation between 2-aminothiophenol and substituted benzaldehydes. Attractive features of

Antidiabetic potential and enzyme kinetics of benzothiazole derivatives and their non-bonded interactions with α-glucosidase and α-amylase

Benzothiazole derivatives were synthesized and their antidiabetic potential evaluated using α-glucosidase, α-amylase, non-enzymatic glycosylation of hemoglobin and advanced glycation end product inhibition assays. Compound 3l showed low IC50 va

An efficient copper(II)-catalyzed synthesis of benzothiazoles through intramolecular coupling-cyclization of N-(2-chlorophenyl)benzothioamides

A wide range of 2-aryl or 2-alkyl-substituted benzothiazoles are synthesized through intramolecular C(aryl)-S bond forming-cyclization using copper(II)-BINAM-catalyzed coupling of less reactive N-(2-chlorophenyl) benzo or alkylthioamide under mild reaction conditions (82 °C).

Synthesis and electronic absorption and fluorescence of 2-arylbenzothiazole derivatives

A series of new 2-arylbenzothiazoles have been prepared in high yields by Jacobson's cyclization condensation of 2-aminobenzenethiol with benzoyl chloride or benzaldehyde derivatives under three different routes. These compounds have been fully characterized by EA, IR, NMR and MS. The electronic absorption and fluorescence of these compounds have been systematically investigated for the first time. The relationships between their photophysical properties and structures have been discussed. The alteration of absorption and emission wavelengths can be elucidated by Hammett's substituent constants.

Copper containing nanosilica thioalated dendritic material: A recyclable catalyst for synthesis of benzimidazoles and benzothiazoles

In this paper, the design and characterization of a new heterogeneous catalyst by incorporation of copper ions into the nanosilica modified by thiole–based dendrimer are reported. The prepared catalyst was characterized by FT–IR, TGA, elemental analysis,

Synthesis and characterization of Cu(II) containing nanosilica triazine dendrimer: A recyclable nanocomposite material for the synthesis of benzimidazoles, benzothiazoles, bis-benzimidazoles and bis-benzothiazoles

The present study describes the synthesis, characterization, and catalytic activity of Cu(II) containing nanosilica triazine dendrimer (Cu(II)-TD@nSiO 2). The prepared catalyst was characterized by FT-IR, TGA, elemental analysis, UV-vis, FE-SEM

Synthesis, catalytic activity and phytotoxicity of a supported nickel(II) Schiff base complex

A supported Ni(II) complex has been synthesized and characterized by FTIR, UV-vis diffuse reflectance spectroscopy, thermogravimetric analysis and scanning electron microscopy. Its catalytic activity was evaluated for alkyne-azide coupling and benzothiazo

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.

Formation of a nanorod shaped ionogel and its high catalytic activity for one-pot synthesis of benzothiazoles

An ionogel was synthesized through the confinement of 1,3,5-trimethyl pyrazolium chloride as an ionic liquid in a silica-gel matrix through a sol-gel process, and its catalytic activity was compared with a silica supported ionic liquid for the synthesis of benzothiazoles using 2-aminothiophenol and aldehydes/ketones. The reaction between 3-methoxyacetophenone and 2-aminothiophenol produced 2-(3-methoxyphenyl)benzothiazole, and its structure was determined using X-ray crystallography. The ionogel was characterized with SEM, TEM, FTIR and TGA.

Elemental Sulfur-Mediated Decarboxylative Redox Cyclization Reaction: Copper-Catalyzed Synthesis of 2-Substituted Benzothiazoles

A S 8 -mediated directed decarboxylative redox-cyclization strategy for the synthesis of 2-substituted benzothiazoles from o -iodoanilines, arylacetic acids, and elemental sulfur catalyzed by cheap copper metal has been developed. This reaction is operationally simple, ligand-free, compatible with a wide range of functional groups, and provides the desired products in good to excellent yields. In addition, a gram-scale experiment was carried out to furnish PMX 610, an antitumor drug.

Synthesis, characterization, and applications of novel Co(II)-pyridoxal phosphate-Schiff base/SBA-15 as a nanocatalyst for the green synthesis of benzothiazole heterocycles

Mesoporous heterogeneous santa barbara amorphous (SBA)-15-supported cobalt complex, as a novel nanocatalyst containing N–O chelating Schiff-base ligand was successfully synthesized by the reaction of SBA-15 and Cobalt(II)-Schiff-base complex. The Co(II)-S

One-pot copper-catalyzed synthesis of 2-substituted benzothiazoles from 2-iodoanilines, benzyl chlorides and elemental sulfur

An efficient one-pot three-component reaction of 2-iodoanilines, benzyl chlorides and elemental sulfur to form 2-substituted benzothiazoles in satisfactory yields (up to 98%) has been described. The reaction tolerated a wide range of functional groups on the aromatic ring. And heterocycle methylene chlorides substrates were also found to be compatible.

Synthesis of 2-Arylbenzothiazoles by Copper-Catalyzed One-Pot Three-Component Reactions in Water

Copper-catalyzed three-component reactions of 2-iodoanilines, benzylamines, and sulfur powder are reported to afford benzothiazoles in a simple one-pot procedure by using water as solvent. A variety of 2-arylbenzothiazoles were obtained in moderate to good yields up to 88%.

One-pot tandem approach for the synthesis of benzothiazoles from benzyl halides

A one-pot tandem approach for the synthesis of benzothiazoles from benzyl halides and o-aminobenzenethiol was described. Benzothiazoles were obtained in high chemical yields under mild conditions in DMSO in the absence of an additional oxidant. Both benzy

Cuprous cluster as effective single-molecule metallaphotocatalyst in white light-driven C[sbnd]H arylation

This study investigated a series of ferrocenyltelluroether based cuprous halide clusters as effective single-molecule metallaphotocatalysts (SMP) in white light-driven C[sbnd]H arylation at room temperature and air. A systematic mechanistic study reveals that Cu(I) cluster can be irradiated by visible light to promote proton-coupled electron transfer (PCET), during which the electron from Cu(I)* leaves together with the proton from benzothiazole C[sbnd]H, leading to the formation of benzothiazolate-coordinated Cu(II) intermediate and aryl radical. Subsequently, the electron transfer (ET) from the ferrocene unit to the Cu(II) center releases the reactive benzothiazolate to form the target product with aryl radical. The advantages of these copper(I) halide clusters as SMP include high photocatalytic efficiency, structure adjustability, mild reaction conditions and good functional group tolerance.

PTSA catalyzed simple and green synthesis of benzothiazole derivatives in water

p-Toluenesulfonic acid (10 mol%) was found to be an effective and efficient catalyst for the synthesis of 2-substituted benzothiazoles from aromatic aldehydes and 2-aminothiophenol in moderate to excellent yields in water. This method provides a simple an

Synthesis of 2-aryl-benzothiazoles via Ni-catalyzed coupling of benzothiazoles and aryl sulfamates

2-Aryl-benzothiazoles have been successfully synthesized via a simple coupling reaction between benzothiazoles and aryl sulfamates using a nickel catalyst. The nickel catalyst is inexpensive, reusable and commercially available. In addition, the use of highly expensive palladium catalysts and unstable raw materials has been avoided. 2-Aryl-benzothiazoles bearing various substituents on the aryl groups were obtained in good yield.

Atom economic palladium catalyzed novel approach for arylation of benzothiazole and benzoxazole with triarylbismuth reagents via C[sbnd]H activation

We have developed a novel method for the direct C[sbnd]H functionalization of benzothiazole and benzoxazole using triarylbismuth reagents. The arylation proceeds using the homogeneous catalytic system PdCl2, Cu(OAc)2 and PPh3 ligand. Triarylbismuthines, which act as threefold arylating reagents, have low toxicity, are green and ecofriendly. These methodologies are particularly useful to prepare arylated benzothiazoles and benzoxazoles.

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.

Ultrafine Pt nanoparticles supported on a dendrimer containing thiol groups: An efficient catalyst for the synthesis of benzimidazoles and benzothiazoles from benzyl alcohol derivatives in water

A novel and unique platform was prepared based on a dendrimer containing thiol groups supported on nanosilica (nSTDP), and ultrafine platinum nanoparticles were synthesized and immobilized on the thiol decorated branches of nSTPD. The new catalyst, (Ptnp?nSTDP), was characterized by different techniques such as FE-SEM, TEM, ICP, XPS and DR UV-vis. This heterogeneous catalyst presented an outstanding performance for the synthesis of benzimidazole and benzothiazole derivatives through a reaction between benzyl alcohol derivatives and 2-aminothiophenol or 1,2-phenylenediamine. No requirement for the pre-reduction of catalysts and using water as a green solvent make it an individual catalyst for these reactions. Furthermore, the catalyst can be easily recovered and reused five consecutive times in the production of benzimidazoles and benzothiazoles without significant leaching of Pt and loss of its activity which illustrated the chemical stability of the catalyst during the reaction.

Tuning the Excited State of Tetradentate Pd(II) and Pt(II) Complexes through Benzannulated N-Heteroaromatic Ring and Central Metal

A series of tetradentate Pd(II) and Pt(II) complexes containing fused 5/6/6 metallocycles with phenyl N-heteroaromatic benzo[d]imidazole (pbiz), benzo[d]oxazole (pboz) or benzo[d]thiazole (pbthz)-containing ligands was developed. Systematic studies by exp

Diversity in Heterocycle Synthesis Using α-Iminocarboxylic Acids: Decarboxylation Dichotomy

Despite the structural similarity with imines, α-iminocarboxylic acids have seldom been used in heterocycles synthesis. The reactions of ortho-substituted anilines and arylglyoxylic acids in DMSO at 40 °C gave various benzo-fused five- to six-membered N-heterocycles in good to excellent yields. The reaction proceeds via intramolecular Michael addition of α-iminocarboxylic acids, generated in situ, with an ortho-substituted nucleophile, yielding an isolable unprecedented tetrahedral carboxylic acids, which upon decarboxylation without any aid of additional reagents forms the N-heterocycles. DMSO is crucial in this reaction, perhaps because of improved solubility and the ease of decarboxylation of these tetrahedral carboxylic acids. However, a copper-catalyzed reaction of ortho-substituted anilines and 2-bromoarylglyoxylic acids gave a dibenzo-fused seven-membered N-heterocycle under a basic reaction condition. Unlike intramolecular cyclization with α-iminocarboxylic acids in the first case, α-iminocarboxylic acid undergoes a competitive decarboxylation under the copper-catalyzed conditions, which upon subsequent heteroarylation form the heterocycles. Taken together, the study described herein represents two different modes of decarboxylation observed with α-iminocarboxylic acids, leading to the synthesis of divergent heterocycles and pharmaceuticals, which remained unexplored previously.