42474-60-2

Usage

Uses

Used in Organic Synthesis:
6-Benzothiazolecarbonitrile,2-methyl-(9CI) serves as a valuable building block in the synthesis of a wide range of organic compounds. Its versatile structure allows for the formation of various derivatives, making it a promising candidate for the development of new chemical entities.
Used in Material Science:
Due to its distinct molecular properties, 6-Benzothiazolecarbonitrile,2-methyl-(9CI) can be utilized in the development of advanced materials with specific characteristics. Its potential applications in material science may include the creation of novel polymers, coatings, or other functional materials.
Used in Pharmaceutical Industry:
6-Benzothiazolecarbonitrile,2-methyl-(9CI) may exhibit biological activity, making it a candidate for further exploration as a pharmaceutical agent. Its unique structure could potentially be harnessed to develop new drugs with therapeutic benefits. However, additional research and experimentation are required to fully understand its potential as a medicinal compound and to optimize its properties for specific applications.

InChI:InChI=1/C9H6N2S/c1-6-11-8-3-2-7(5-10)4-9(8)12-6/h2-4H,1H3

Upstream product

• 29277-45-0 4-cyanothioacetanilide 
• 2941-62-0 6-amino-2-methylbenzothiazole 
• 143-33-9 sodium cyanide 
• 557-21-1 zinc(II) cyanide 
• 4146-24-1 6-chloro-2-methylbenzo[d]thiazole 
• 35704-19-9 N-(4-cyanophenyl)acetamide 
• 120-75-2 2-Methylbenzothiazole 
• 2941-63-1 2-methyl-6-nitrobenzothiazole 
• 151-50-8 potassium cyanide 

Downstream Products

• 6941-28-2 2-methyl-1,3-benzothiazole-6-carboxylic acid 
• 99358-50-6 2-methyl-benzothiazole-6-carboxylic acid hydrazide 
• 101117-74-2 N-benzoyl-N'-(2-methyl-benzothiazole-6-carbonyl)-hydrazine 
• 1024016-49-6 2-[(E)-2-(4-pyrrolidin-1-ylphenyl)vinyl]benzothiazole-6-carbonitrile 
• 1024016-50-9 2-{(E,E)-4-[4-(dimethylamino)phenyl]buta-1,3-dien-1-yl}benzothiazole-6-carbonitrile 
• 1024016-48-5 2-{(E)-2-[4-(diphenylamino)phenyl]vinyl}benzothiazole-6-carbonitrile 
• 167979-41-1 2-[4-(1-tert-butoxycarbonyl-pyrrolidin-3-yloxy)-phenyl]-2-(6-cyano-benzothiazol-2-ylmethyl)-malonic acid diethyl ester 
• 167979-54-6 2-(bromomethyl)-1,3-benzothiazole-6-carbonitrile 

Relevant academic research and scientific papers

Recyclable copper-catalyzed cyclization of o-haloanilides and metal sulfides: An efficient and practical access to substituted benzothiazoles

An efficient heterogeneous copper-catalyzed cyclization of o-haloanilides and metal sulfides has been achieved via the C–S coupling in DMF at 80 or 140 °C in the existence of an MCM-41-bound NHC-Cu(I) catalyst and then intramolecular condensation, delivering a wide range of substituted benzothiazoles in mostly good to high yields. This new MCM-41-NHC-CuI complex can facilely be obtained by a two-step procedure starting from easily accessible and inexpensive reagents and reused more than seven times without any significant loss of its catalytic efficiency. The present protocol has been successfully applied to the gram-scale synthesis of two antitumor agents 5F203 and PMX 610.

A room temperature cyanation of (hetero)aromatic chlorides by an air stable nickel(II) XantPhos precatalyst and Zn(CN)2

A methodology for the synthesis of (hetero)aromatic nitriles from aryl chlorides at room temperature has been developed. This methodology uses an air and moisture stable nickel(ii) XantPhos precatalyst and Zn(CN)2 as the cyanide (CN-) source.

Preparation of novel push-pull benzothiazole derivatives with reverse polarity: Compounds with potential non-linear optic application

The hitherto unknown 6-dimethylaminobenzothiazole-2-carbaldehyde was prepared as a starting compound for the synthesis of novel push-pull benzothiazole derivatives with reverse polarity. These compounds are substituted at the 2-position by strong electron-acceptor groups and at the 6-position by NMe2 as strong electron-donor. The new method for synthesis of 6-dimethylaminobenzothiazole involved the successful use of sonochemical reductive methylation. Expected non-linear optical properties of target molecules were studied by EFISH method.

Synthesis, crystal structure and antiproliferative evaluation of some new substituted benzothiazoles and styrylbenzothiazoles

The multistep synthesis of a series of new substituted-benzothiazoles as hydrochloride or quaternary salts is described. 6-Amidino substituted 2-aminobenzothiazoles (5, 6), N-methyl-2-(4-cyanostyryl)benzothiazolium iodide (8), cyano-substituted-2-styrylbenzothiazoles (9-11) and amidino and bis-amidino-substituted 2-styrylbenzothiazoles (12-17) were prepared. The crystal structure of amidino derivative (6) was determined by single crystal X-ray analysis. All new prepared compounds were tested on the cytostatic activities against malignant cell lines: (SW620, colon carcinoma; Hep2, laryngeal carcinoma; HBL, melanoma; HeLa, cervical carcinoma and WI38, human normal fibroblasts). The compounds exerted a different inhibitory effect, depended on concentration and type of the cells. The best inhibitory effect was achieved with compounds (12-15), with slight differences among them. All of them inhibited the growth of examined tumor cell lines and also normal fibroblasts. Other examined compounds exhibited a moderate inhibitory effect, depending on type of the cells. Majority of them inhibited the growth of HeLa cells and WI38.