219766-02-6

Basic information

• Product Name: 2-(METHYLTHIO)NICOTINONITRILE
• Synonyms: 2-(METHYLTHIO)NICOTINONITRILE;3-Pyridinecarbonitrile,2-(methylthio)-(9CI);2-(methylsulfanyl)pyridine-3-carbonitrile
• CAS NO: 219766-02-6
• Molecular Formula: C7H6N2S
• Molecular Weight: 150.2
• Product Categories: PYRIDINE;NITRILE
• Mol File: 219766-02-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 282.9°Cat760mmHg
• Flash Point: 124.9°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 0.00327mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: 2-(METHYLTHIO)NICOTINONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(METHYLTHIO)NICOTINONITRILE(219766-02-6)
• EPA Substance Registry System: 2-(METHYLTHIO)NICOTINONITRILE(219766-02-6)

Safety Data

• Hazardous Substances Data: 219766-02-6(Hazardous Substances Data)

Usage

General Description

2-(Methylthio)nicotinonitrile is a chemical compound with the molecular formula C7H7NOS. It is a derivative of nicotinonitrile with a methylthio group attached to the 2-position of the pyridine ring. 2-(METHYLTHIO)NICOTINONITRILE is commonly used in organic synthesis and pharmaceutical research as a building block for the preparation of various biologically active molecules. It is also a potential intermediate in the synthesis of novel heterocyclic compounds with potential pharmacological properties. Additionally, 2-(Methylthio)nicotinonitrile has been studied for its potential anti-cancer and anti-inflammatory properties, making it a subject of interest in medicinal chemistry research.

InChI:InChI=1/C7H6N2S/c1-10-7-6(5-8)3-2-4-9-7/h2-4H,1H3

Upstream product

• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 5188-07-8 sodium thiomethoxide 
• 616-38-6 carbonic acid dimethyl ester 

Relevant articles and documents

Palladium-Catalyzed Thiomethylation via a Three-Component Cross-Coupling Strategy

In this report, the combination of masked inorganic sulfur and dimethyl carbonate was designed to achieve thiomethylated cross coupling of aryl chlorides. Remarkably, this powerful strategy realized thiomethylation of nucleosides bearing unprotected ribose, chloride-containing pharmaceuticals with late-stage coupling, and herbicides possessing multiple heteroatoms and steric hindrance. Moreover, this protocol is practically amenable to multigram-scale synthesis with a lower catalysis loading and a higher yield.

Pd- and Ni-catalyzed cross-coupling reactions of functionalized organozinc reagents with unsaturated thioethers

A variety of unsaturated thioethers have been subjected to cross-coupling reactions with functionalized zinc reagents in the presence of a transition-metal catalyst. Three different catalytic systems based on Pd(OAc)2 or [Ni(acac)2] and the ligands S-Phos or DPE-Phos gave the best results. N-Heterocyclic thioethers based on a pyridine, pyrimidine, pyrazine, pyridazine, triazine, benzothiazole, benzoxazole, pyrrole, or quinazoline ring, as well as thiomethylacetylenes, serve as electrophiles in this cross-coupling reaction. Aryl-, heteroaryl-, benzylic, and alkylzinc halides with sensitive functionalities, such as ester, nitrile, or ketone groups react at ambient temperature with unsaturated thioethers using a Ni catalyst. The corresponding Pd-catalyzed reactions require slightly higher temperatures. Large-scale cross-coupling experiments (10-20 mmol) with N-heterocycles are also reported.

Pd-catalyzed cross-coupling of functionalized organozinc reagents with thiomethyl-substituted heterocycles

Various thiomethyl-substituted N-heterocycles (pyridines, pyrimidines, pyrazines, pyridazines, triazines, benzothiazoles, benzoxazoles, pyrazoles, benzindazoles, quinazolines, etc.) undergo smooth Pd-catalyzed cross-coupling reactions with functionalized