5633-57-8

Basic information

• Product Name: Benzene,1-methoxy-4-(phenylthio)-
• Synonyms: Benzene,1-methoxy-4-(phenylthio)-
• CAS NO: 5633-57-8
• Molecular Formula: C₁₃H₁₂OS
• Molecular Weight: 216.3
• Mol File: 5633-57-8.mol
• Article Data: 291

Chemical Properties

• Boiling Point: 350.7°Cat760mmHg
• Flash Point: 165.9°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 8.73E-05mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: Benzene,1-methoxy-4-(phenylthio)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene,1-methoxy-4-(phenylthio)-(5633-57-8)
• EPA Substance Registry System: Benzene,1-methoxy-4-(phenylthio)-(5633-57-8)

Safety Data

• Hazardous Substances Data: 5633-57-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H12OS/c1-14-11-7-9-13(10-8-11)15-12-5-3-2-4-6-12/h2-10H,1H3

Upstream product

• 696-62-8 para-iodoanisole 
• 930-69-8 sodium thiophenolate 
• 591-50-4 iodobenzene 
• 696-63-9 4-Methoxybenzenethiol 
• 80816-33-7 C₂₀H₁₉NO₃S₂ 
• 80816-33-7 C₂₀H₁₉NO₃S₂ 
• 7205-58-5 ethyl (4-methoxyphenyl) sulfide 
• 118-92-3 anthranilic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 108-98-5 thiophenol 
• 100-66-3 methoxybenzene 
• 882-33-7 diphenyldisulfane 
• 56-23-5 tetrachloromethane 
• 21122-37-2 S-phenyl 4-methoxybenzothioate 

Downstream Products

• 53279-48-4 C₁₄H₁₃ClOS 
• 106-41-2 4-bromo-phenol 
• 882-33-7 diphenyldisulfane 
• 97361-14-3 1-(4-((4-methoxyphenyl)thio)phenyl)ethan-1-one 
• 53279-50-8 2-[4-[(4-methoxyphenyl)thio]phenyl]ethylamine 
• 53279-51-9 4-[[4-(2-aminoethyl)phenyl]thio]phenol 
• 53279-49-5 [4-(4-Methoxy-phenylsulfanyl)-phenyl]-acetonitrile 
• 931-59-9 benzenesulfenyl chloride 
• 7402-69-9 p-hydroxyphenyl p-tolyl sulfone 
• 74-88-4 methyl iodide 
• 3112-84-3 4-methoxyphenyl phenyl sulfone 
• 5633-55-6 4-phenylsulfanylphenol 
• 127279-74-7 (4-methoxyphenyl)diphenylsulfonium hexafluoroantimonate 
• 951-92-8 1-methoxyl-4-(phenylsulfinyl)benzene 

Relevant articles and documents

Evidence for a mono-electron transfer process in the BF3-promoted reaction of 4'-nitrobenzenesulphenanilide (NBSA)

ESR spectroscopy shows the formation of a radical species in the BF3-promoted reaction of NBSA, an acid/base Lewis-type reaction.

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.

Regioselective C-H Thioarylation of Electron-Rich Arenes by Iron(III) Triflimide Catalysis

A mild and regioselective method for the preparation of unsymmetrical biaryl sulfides using iron(III) catalysis is described. Activation of N-(arylthio)succinimides using the powerful Lewis acid iron(III) triflimide allowed the efficient thiolation of a range of arenes, including anisoles, phenols, acetanilides, and N-heterocycles. The method was applicable for the late-stage thiolation of tyrosine and tryptophan derivatives and was used as the key step for the synthesis of pharmaceutically relevant biaryl sulfur-containing compounds such as the antibiotic dapsone and the antidepressant vortioxetine. Kinetic studies revealed that while N-(arylthio)succinimides bearing electron-deficient arenes underwent thioarylation catalyzed entirely by iron(III) triflimide, N-(arylthio)succinimides with electron-rich arenes displayed an autocatalytic mechanism promoted by the Lewis basic product.