22190-12-1

Basic information

• Product Name: 2-(PHENYLTHIO)QUINOLINE
• Synonyms: 2-(phenylthio)-quinolin;2-(PHENYLTHIO)QUINOLINE;2-(Phenylthio)quinoline,98%
• CAS NO: 22190-12-1
• Molecular Formula: C₁₅H₁₁NS
• Molecular Weight: 237.32
• EINECS: 244-828-2
• Mol File: 22190-12-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 48 °C
• Boiling Point: 408.1°C at 760 mmHg
• Flash Point: 200.6°C
• Appearance: /
• Density: 1.1568 (rough estimate)
• Vapor Pressure: 1.69E-06mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• CAS DataBase Reference: 2-(PHENYLTHIO)QUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(PHENYLTHIO)QUINOLINE(22190-12-1)
• EPA Substance Registry System: 2-(PHENYLTHIO)QUINOLINE(22190-12-1)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 22190-12-1(Hazardous Substances Data)

Usage

General Description

2-(Phenylthio)quinoline, also known as PTQ, is an organic compound that consists of a quinoline core with a phenylthio group attached at the 2-position. It is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals due to its unique properties, such as its ability to act as a ligand for metal catalysis. PTQ has also been studied for its potential anti-malarial and anti-cancer properties. Additionally, PTQ derivatives have been investigated for their potential use as fluorescent probes in biological and materials science research. However, due to its phenylthio group, PTQ should be handled and used with caution, as thiophenol and its derivatives are known to be toxic and may cause irritation to the skin and respiratory system.

InChI:InChI=1/C15H11NS/c1-2-7-13(8-3-1)17-15-11-10-12-6-4-5-9-14(12)16-15/h1-11H

Upstream product

• 612-62-4 2-Chloroquinoline 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 13133-62-5 thiophenolate 
• 6560-83-4 2-iodoquinoline 
• 882-33-7 diphenyldisulfane 
• 2005-43-8 2-bromoquinoline 
• 4551-15-9 phenylthiotrimethylsilane 

Downstream Products

• 24667-94-5 2-(4-methylphenyl)quinoline 
• 34243-33-9 2-thiophen-2-yl-quinoline 
• 506421-62-1 2-(4-(trifluoromethyl)phenyl)-quinoline 
• 64495-58-5 2-benzenesulfonyl-quinoline 

Relevant articles and documents

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PRODUCTION METHOD FOR BI(HETERO)ARYL(THIO)ETHER COMPOUND

PROBLEM TO BE SOLVED: To provide a method for synthesizing a bi(hetero)aryl(thio)ether compound at low cost without discharging halogen-derived waste. SOLUTION: The production method includes, for example as shown in the following formula, reacting a (thio)ester compound represented by formula (1) in the presence of a nickel catalyst (or a palladium catalyst) as well as a ligand compound to produce bi(hetero)aryl(thio)ether compound represented by formula (2). [Ar and Ar' are each independently a substituted/unsubstituted aryl group or heteroaryl group; Y is O or S.]. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Thioetherification of Chloroheteroarenes: A Binuclear Catalyst Promotes Wide Scope and High Functional-Group Tolerance

A constrained binuclear palladium catalyst system affords selective thioetherification of a wide range of functionalized arenethiols with chloroheteroaromatic partners with the highest turnover numbers (TONs) reported to date and tolerates a large variety of reactive functions. The scope of this system includes the coupling of thiophenols with six- and five-membered 2-chloroheteroarenes (i.e., functionalized pyridine, pyrazine, quinoline, pyrimidine, furane, and thiazole) and 3-bromoheteroarenes (i.e., pyridine and furane). Electron-rich congested thiophenols and fluorinated thiophenols are also suitable partners. The coupling of unprotected amino-2-chloropyridines with thiophenol and the successful employment of synthetically valuable chlorothiophenols are described with the same catalyst system. DFT studies attribute the high performance of this binuclear palladium catalyst to the decreased stability of thiolate-containing resting states. Palladium loading was as low as 0.2 mol %, which is important for industrial application and is a step forward in solving catalyst activation/deactivation problems.