16928-73-7

Basic information

• Product Name: Phenyl(triphenylmethyl) sulfide
• Synonyms: Phenyl(triphenylmethyl) sulfide;Phenyltrityl sulfide;Tritylphenyl sulfide
• CAS NO: 16928-73-7
• Molecular Formula: C₂₅H₂₀S
• Molecular Weight: 352.49
• Mol File: 16928-73-7.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Phenyl(triphenylmethyl) sulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl(triphenylmethyl) sulfide(16928-73-7)
• EPA Substance Registry System: Phenyl(triphenylmethyl) sulfide(16928-73-7)

Safety Data

• Hazardous Substances Data: 16928-73-7(Hazardous Substances Data)

Upstream product

• 926-67-0 O-Ethyl thioacetate 
• 981-18-0 triphenyl(phenylazo)methane 
• 16516-12-4 Monothiomalonsaeure-O,O-diethylester 
• 882-33-7 diphenyldisulfane 
• 71-43-2 benzene 
• 341-02-6 trityl tetrafluoroborate 
• 6163-58-2 tris-(o-tolyl)phosphine 
• 930-69-8 sodium thiophenolate 
• 76-83-5 trityl chloride 
• 118487-17-5 2-(4'-toluenesulphonyl)tetrahydro-2H-pyran 
• 536-57-2 p-toluene sulfinic acid 
• 32812-89-8 bis(benzenethiolato)lead(II) 
• 118487-18-6 2,2-(bisphenylthio)tetrahydropyran 
• 4303-71-3 triphenylmethyl sodium 

Downstream Products

• 76-84-6 triphenylmethyl alcohol 
• 882-33-7 diphenyldisulfane 
• 108-98-5 thiophenol 
• 427-36-1 trityl fluoride 
• 1596-25-4 N-tritylacetamide 
• 86774-16-5 W(CO)5((C₆H₅)3CS(C₆H₅)) 
• 1528-27-4 triphenylmethyl potassium 

Relevant articles and documents

FLP reactivity of [Ph3C]+ and (: O -tolyl)3P and the capture of a Staudinger reaction intermediate

The frustrated Lewis pair (FLP) derived from the trityl cation and (o-tolyl)3P effects the activation of 1,4-cyclohexadiene and 1-bromo-4-ethynylbenzene and heterolytically cleaves the S-S bond of diphenyl disulfide. The FLP also captures pentafluorophenyl azide as the Staudinger reaction intermediate, a species that reacts with Ph3SiH to give the silyl analog.

Zinc Chloride Mediated Nucleophilic Substitution: Amination and Thioetherification of Alcohols at Room Temperature

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Structural and solvent effects on the C-S bond cleavage in aryl triphenylmethyl sulfide radical cations

Steady-state and laser flash photolysis (LFP) studies of a series of aryl triphenylmethyl sulfides [1, 3,4-(CH3O)2-C 6H3SC(C6H5)3; 2, 4-CH3O-C6H4SC(C6H5) 3; 3, 4-CH3-C6H4SC(C 6H5)3; 4, C6H5SC(C 6H5)3; and 5, 4-Br-C6H 4SC(C6H5)3] has been carried out in the presence of N-methoxyphenanthridinium hexafluorophosphate in CH 3CN, CH2Cl2, CH2Cl 2/CH3CN, and CH2Cl2/CH3OH mixtures. Products deriving from the C-S bond cleavage in the radical cations 1?+-5?+ have been observed in the steady-state photolysis experiments. Time-resolved LFP showed first-order decay of the radical cations accompanied by formation of the triphenylmethyl cation. A significant decrease of the C-S bond cleavage rate constants was observed by increasing the electron-donating power of the arylsulfenyl substituent, that is, by increasing the stability of the radical cations. DFT calculations showed that, in 2?+ and 3?+, charge and spin densities are mainly localized in the ArS group. In the TS of the C-S bond cleavage an increase of the positive charge in the trityl moiety and of the spin density on the ArS group is observed. The higher delocalization of the charge in the TS as compared to the initial state is probably at the origin of the observation that the C-S bond cleavage rates decrease by increasing the polarity of the solvent.