51238-46-1

Basic information

• Product Name: 4-(phenylsulfanyl)benzonitrile
• Synonyms: 4-(phenylsulfanyl)benzonitrile
• CAS NO: 51238-46-1
• Molecular Formula: C₁₃H₉NS
• Molecular Weight: 211.29
• Mol File: 51238-46-1.mol
• Article Data: 98

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(phenylsulfanyl)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(phenylsulfanyl)benzonitrile(51238-46-1)
• EPA Substance Registry System: 4-(phenylsulfanyl)benzonitrile(51238-46-1)

Safety Data

• Hazardous Substances Data: 51238-46-1(Hazardous Substances Data)

Usage

General Description

4-(phenylsulfanyl)benzonitrile, also known as phenylthio)benzonitrile, is a chemical compound consisting of a benzene ring with a sulfanyl (-S-) group and a nitrile (-CN) group attached to it. It is a yellow to brown crystalline solid with a molecular formula of C13H9NS and a molecular weight of 215.29 g/mol. 4-(phenylsulfanyl)benzonitrile is commonly used in organic synthesis and pharmaceutical research as a building block for the production of various organic compounds. It is also used as a precursor in the synthesis of biologically active molecules and is found in some commercial products. Additionally, 4-(phenylsulfanyl)benzonitrile has potential applications in the development of new materials and as a reagent in chemical reactions.

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 13133-62-5 thiophenolate 
• 930-69-8 sodium thiophenolate 
• 52599-10-7 (4-bromo-phenyl)-phenylsulfanyl-diazene 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 623-00-7 4-bromobenzenecarbonitrile 
• 3058-39-7 4-iodobenzonitrile 
• 17314-33-9 tributyltin phenyl sulfide 
• 111278-47-8 C₁₃H₉N₃S 
• 13435-20-6 tetraethylammoniumcyanide 
• 132555-11-4 (E)-(4-Cyanophenyl)azo phenyl sulfide 
• 2252-32-6 4-cyanophenyldiazonium tetrafluoroborate 
• 619-72-7 4-nitrobenzonitrile 
• 138373-10-1 4-cyanophenyl mesylate 

Downstream Products

• 100723-92-0 N’-hydroxy-4-(phenylthio)benzimidamide 
• 646517-01-3 C₃₀H₂₀N₂O₂S₂ 
• 850566-84-6 C₄₂H₅₂N₂O₂S₂ 
• 84212-05-5 4-phenylthiobenzylamine 
• 618909-31-2 4-(phenylsulfinyl)benzonitrile 
• 28525-13-5 4-(phenylsulfonyl)benzonitrile 
• 65085-83-8 4'-(phenylsulfonyl)acetophenone 
• 4779-37-7 2-bromo-1-(4-(phenylsulfonyl)phenyl)ethan-1-one 
• 2920-38-9 4-cyano-1,1'-biphenyl 

Relevant articles and documents

Electrochemistry Enabled Nickel-Catalyzed Selective C?S Bond Coupling Reaction

This work describes an electrochemical enabled nickel-catalyzed chemoselective C?S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C?S bond coupling has demonstrated excellent redox activity, scalability and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.

A Visible-Light-Harvesting Covalent Organic Framework Bearing Single Nickel Sites as a Highly Efficient Sulfur–Carbon Cross-Coupling Dual Catalyst

Covalent Organic Frameworks (COFs) have recently emerged as light-harvesting devices, as well as elegant heterogeneous catalysts. The combination of these two properties into a dual catalyst has not yet been explored. We report a new photosensitive triazine-based COF, decorated with single Ni sites to form a dual catalyst. This crystalline and highly porous catalyst shows excellent catalytic performance in the visible-light-driven catalytic sulfur–carbon cross-coupling reaction. Incorporation of single transition metal sites in a photosensitive COF scaffold with two-component synergistic catalyst in organic transformation is demonstrated for the first time.

Dimsyl Anion Enables Visible-Light-Promoted Charge Transfer in Cross-Coupling Reactions of Aryl Halides

A methodology is reported for visible-light-promoted synthesis of unsymmetrical chalcogenides enabled by dimsyl anion in the absence of transition-metals or photoredox catalysts. The cross-coupling reaction between aryl halides and diaryl dichalcogenides proceeds with electron-rich, electron-poor, and heteroaromatic moieties. Mechanistic investigations using UV-Vis spectroscopy, time-dependent density functional theory (TD-DFT) calculations, and control reactions suggest that dimsyl anion forms an electron-donor-acceptor (EDA) complex capable of absorbing blue light, leading to a charge transfer responsible for generation of aryl radicals from aryl halides. This previously unreported mechanistic pathway may be applied to other light-induced transformations performed in DMSO in the presence of bases and aryl halides.