35620-68-9

Usage

Uses

Used in Organic Synthesis:
2-(PHENYLTHIO)NICOTINONITRILE is used as a building block in organic synthesis for its ability to contribute to the formation of complex molecular structures. Its unique combination of functional groups allows for a wide range of chemical reactions, facilitating the creation of new compounds with diverse properties.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-(PHENYLTHIO)NICOTINONITRILE is utilized as a key component in drug discovery and development. Its potential biological activities, such as acting as a ligand for receptors and enzymes, make it a promising candidate for the design of novel therapeutic agents.
Used in the Production of Pharmaceuticals:
2-(PHENYLTHIO)NICOTINONITRILE serves as a starting material in the synthesis of various pharmaceuticals. Its versatility and reactivity enable the development of a broad spectrum of medicinal compounds, contributing to the advancement of treatments for numerous diseases and conditions.
Used in Agrochemicals:
2-(PHENYLTHIO)NICOTINONITRILE also finds application in the agrochemical sector, where it is employed as a precursor in the synthesis of pesticides and other agricultural chemicals. Its potential role in enhancing crop protection and yield makes it a valuable asset in this industry.
Overall, 2-(PHENYLTHIO)NICOTINONITRILE is a multifaceted chemical with applications spanning across various industries, particularly in the development of new chemical entities for pharmaceutical and agrochemical uses.

InChI:InChI=1/C12H8N2S/c13-9-10-5-4-8-14-12(10)15-11-6-2-1-3-7-11/h1-8H

Upstream product

• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 108-98-5 thiophenol 

Downstream Products

• 1283024-41-8 ethyl 3-[(3-cyanopyridin-2-yl)methyl]benzoate 
• 1283024-35-0 2-(2-chlorobenzyl)nicotinonitrile 

Relevant academic research and scientific papers

Palladium-catalyzed heteroaryl thioethers synthesis overcoming palladium dithiolate resting states inertness: Practical road to sulfones and NH-sulfoximines

We provide efficient synthetic access to heteroaryl sulfones in two-steps using a simple palladium–1,1′-bis[(diphenyl)phosphanyl]ferrocene catalyst to form in high yields variously functionalized heteroaromatic thioethers. Pyridinyl-containing substrates can be subsequently selectively oxidized into sulfones and NH-sulfoximines by using very mild oxidation conditions with a high functional group tolerance. In the palladium-catalyzed C–S coupling of heteroaromatic thiols, reactivity limitation is attached with electron-deficient thiols. We show that this limitation can be resolved by the successful use of 2-bromoheteroarenes in the C–S coupling. We established herein that this choice of heteroaryl electrophilic reagent in palladium-catalyzed C–S bond formation allows overcoming palladium dithiolate out-of-cycle resting state inertness. This was illustrated in the stoichiometric reactivity study of the palladium dithiolate formed from 4-trifluoromethylbenzen-1-thiol –isolated and characterized by multinuclear NMR and XRD– with both 2-chloropyridine and 2-bromopyridine.

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.

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.

Catalyst-free and base-free water-promoted SNAr reaction of heteroaryl halides with thiols

A simple and efficient route for the synthesis of biaryl sulfides have been developed in aqueous medium under base- and catalyst-free conditions. A wide variety of heteroaryl halides and thiols underwent SNAr reaction to provide diaryl sulfides in good to excellent yields. The remarkable key features of the reaction include the use of water as an inexpensive and environmentally benign reaction medium, absence of any additional reagent or catalyst, and easy isolation of the products. Georg Thieme Verlag Stuttgart.