85460-29-3

Basic information

• Product Name: 2-Benzothiazoleacetonitrile, a-[(4-chlorophenyl)methylene]-
• CAS NO: 85460-29-3
• Molecular Formula: C16H9ClN2S
• Molecular Weight: 296.78
• Mol File: 85460-29-3.mol

Chemical Properties

• CAS DataBase Reference: 2-Benzothiazoleacetonitrile, a-[(4-chlorophenyl)methylene]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzothiazoleacetonitrile, a-[(4-chlorophenyl)methylene]-(85460-29-3)
• EPA Substance Registry System: 2-Benzothiazoleacetonitrile, a-[(4-chlorophenyl)methylene]-(85460-29-3)

Safety Data

• Hazardous Substances Data: 85460-29-3(Hazardous Substances Data)

Upstream product

• 56278-50-3 2-cyanomethylbenzothiazole 
• 104-88-1 4-chlorobenzaldehyde 
• 137-07-5 2-amino-benzenethiol 
• 1867-38-5 4-chlorobenzylidenemalonodinitrile 
• 1334602-99-1 2-(benzothiazole-2-yl)-3-oxopentanedinitrile 

Downstream Products

• 85460-32-8 1-amino-2-(benzo[d]thiazol-2-yl)-3-(4-chlorophenyl)-3H-benzo[4,5]thiazolo[3,2-a]pyridine-4-carbonitrile 
• 1383625-41-9 3-(5-amino-3-methylisoxazol-4-yl)-2-(benzo[d]thiazol-2-yl)-3-(4-chlorophenyl) propiononitrile 
• 1133846-66-8 3-(4-chlorophenyl)-2,3-dihydro-2,2-diphenyl-1-oxo-1H-pyrido[2,1-b]benzothiazol-4-carbonitrile 
• 603-32-7 triphenyl-arsane 
• 85460-36-2 1-Amino-3-(4-chlorophenyl)-3H-pyrido<2,1-b>benzothiazol-2,4-dicarbonitrile 
• 1132753-53-7 7-amino-6-(benzothiazol-2-yl)-5-(4-chlorophenyl)-2,3-dihydro-2-thioxopyrido[2,3-d]pyrimidin-4H-one 
• 1132753-59-3 C₂₀H₁₄ClN₅OS₂ 

Relevant articles and documents

Benzothiazolopyridine compounds: Facial synthesis, characterization, and molecular docking study on estrogen and progesterone receptors

In this work, a convenient and efficient procedure for the synthesis of 1-amino-2- (benzo [d] thiazol-2-yl)-3-aryl-3-hydro-benzo [4, 5] thiazolo [3, 2-a] pyridine-4-carbonitrile derivatives (6a-f) was studied. This synthesis was catalyzed by piperidine in an ethanol medium under ultrasonic irradiation at room temperature. The obtained results were compared with the conventional reflux method. Compared to the reflux method, ultrasonic irradiation provided several privileges such as shorter reaction time, cleaner reactions, and higher yields. By using the ultrasound technique, the reaction time was reduced from 50- 480 min to 80–200 min and the product yields improved from 10 -71% to 30–90% compared to the reflux method. Molecular docking studies of synthetic compounds (ligands) were carried out with some vital targets in the breast cancers, such as estrogen receptor-α (ERα) and progesterone receptors A and B (PRA and PRB). The main aim of this evaluation was to predict the activity of ligands against ERα, PRA, and PRB. The docking results show that all ligands have favorable interactions with receptors in terms of binding free energy.

Highly diastereoselective synthesis of 3-methylenetetrahydropyrans by palladium-catalyzed oxa-[4 + 2] cycloaddition of 2-alkenylbenzothiazoles

A highly diastereoselective synthesis of 3-methylenetetrahydropyrans via palladium-catalyzed oxa-[4 + 2] cycloaddition of 2-alkenylbenzothiazoles with allyl carbonates bearing a nucleophilic alcohol side chain is presented. This synthetic methodology tolerates a wide variety of 2-alkenylbenzothiazoles and afforded the desired 3-methylenetetrahydropyrans in good yields and excellent dr. In addition, further derivatizations resulted in new scaffolds, making them useful synthetic precursors.

Design, Synthesis, and Anticancer Activity of Novel Benzothiazole Analogues

On the pharmaceutical account of the reported anticancer activity of benzothiazole derivatives, differently substituted benzothiazole derivatives 2a–c to 34a,b, attached at 2-position to different heterocyclic moieties, were synthesized via different chemical reactions. Thirteen of the newly synthesized compounds were selected by the National Cancer Institute, Bethesda, Maryland, USA, and evaluated for their in vitro antitumor activity against 60 human tumor cell lines in a one-dose screening panel among which two compounds 4 and 17 showed high activity and were selected for further evaluation in the five-dose full panel assay, in which compound 4 exerted powerful growth inhibitory activity against all cell lines with GI50 ranging from 0.683 to 4.66?μM/L in addition to excellent lethal activity against most of the cell lines.

A splendid method for synthesis of 2-(benzothiazole)-3-phenyl acrylonitrile derivatives catalysed by piperdine

A simple and efficient method is developed for the synthesis of 2-(benzothiazol-2-yl)-3- (substituted phenyl)acrylonitrile from 2-(benzothiazole-2-yl)-3-oxopentanedinitrile and aromatic aldehydes in the presence of a catalytic amount of piperdine into ethanol at reflux. Advantage of this procedure is relatively good yields (81-86%) with short reaction times (1.5-3 h), under moderate reaction conditions and simple workup procedure, plus easy preparation and handling of the catalyst.

UNCATALYZED KNOEVENAGEL CONDENSATION OF 2-CYANOMETHYLBENZOTHIAZOLE WITH AROMATIC ALDEHYDES. PREPARATION OF 3-ARYL-2-(2-BENZOTHIAZOLYL)-ACRYLONITRILES AND 3-(2-BENZOTHIAZOLYL)-COUMARIN IMINES

A series of 3-aryl-2-(2-benzothiazolyl)-acrylonitriles (3a-n) and 3-(2-benzothiazolyl)-coumarin imines (5a-f) are prepared in good to high yields by refluxing solutions of 2-cyanomethylbenzothiazole (1) and aromatic aldehydes (2, 4) in ethanol. Key words:

Electro-organic Synthesis of some Cyclopentanone Derivatives

The electroreduction of some benzothiazole derivatives in aqueous media has been studied.A mechanism is suggested and discussed for the formation of the cyclopentanone derivatives which were isolated and identified.The mechanism proposed has been confirme

Nitriles in Heterocyclic Synthesis: Novel Synthesis of Pyridobenzothiazoles and 1,3-Benzothiazole Derivatives

Novel synthesis of pyridobenzothiazoles, pyridine, pyran, thiopyran, pyridazine and coumarin derivatives utilising benzothiazol-2-ylacetonitrile, as starting component are reported.