38251-72-8

Basic information

• Product Name: 4-cyanobenzyl(4-bromophenyl)sulfane
• Synonyms: 4-cyanobenzyl(4-bromophenyl)sulfane
• CAS NO: 38251-72-8
• Molecular Weight: 304.21
• Mol File: 38251-72-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-cyanobenzyl(4-bromophenyl)sulfane(CAS DataBase Reference)
• NIST Chemistry Reference: 4-cyanobenzyl(4-bromophenyl)sulfane(38251-72-8)
• EPA Substance Registry System: 4-cyanobenzyl(4-bromophenyl)sulfane(38251-72-8)

Safety Data

• Hazardous Substances Data: 38251-72-8(Hazardous Substances Data)

Upstream product

• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 106-40-1 4-bromo-aniline 
• 106-53-6 para-bromobenzenethiol 
• 17201-43-3 4-cyanobenzyl bromide 

Relevant articles and documents

Aryl alkyl, aryl aryl thioether compound and its synthesis method

The invention discloses a synthesis method of an aryl-alkyl and aryl-aryl thioether compound represented by a formula (III). According to the synthesis method, aryl tetrafluoroboric acid diazonium salt is taken as a reaction raw material in a reaction solvent, aryl and alkyl thiosulfate is taken as a sulfurizing agent, and the materials react under the catalysis action of visible light and a photosensitive agent to obtain the aryl-alkyl and aryl-aryl thioether compound. According to the synthesis method, the raw materials are easy to obtain and are cheap, the reaction operation is simple, the reaction condition is mild and environment-friendly, the yield is higher, the functional group tolerance is excellent, later modification of drugs is successfully realized, and an efficient C-S bond construction method is provided for medicinal chemistry and biological orthogonal chemistry research.

Mechanistic Study of a Photocatalyzed C-S Bond Formation Involving Alkyl/Aryl Thiosulfate

This study presents thioether construction involving alkyl/aryl thiosulfates and diazonium salt catalyzed by visible-light-excited [Ru(bpy)3Cl2] at room temperature in 44-86 % yield. Electron paramagnetic resonance studies found that thiosulfate radical formation was promoted by K2CO3. Conversely, radicals generated from BnSH or BnSSBn (Bn=benzyl) were clearly suppressed, demonstrating the special property of thiosulfate in this system. Transient absorption spectra confirmed the electron-transfer process between [Ru(bpy)3Cl2] and 4-MeO-phenyl diazonium salt, which occurred with a rate constant of 1.69×109 M-1 s-1. The corresponding radical trapping product was confirmed by X-ray diffraction. The full reaction mechanism was determined together with emission quenching data. Furthermore, this system efficiently avoided the over-oxidation of sulfide caused by H2O in the photoexcited system containing Ru2+. Both aryl and heteroaryl diazonium salts with various electronic properties were investigated for synthetic compatibility. Both alkyl- and aryl-substituted thiosulfates could be used as substrates. Notably, pharmaceutical derivatives afforded late-stage sulfuration smoothly under mild conditions.