1058-14-6

Basic information

• Product Name: 4-methyl-N-(triphenylphosphoranylidene)benzenesulfonamide
• Synonyms: 4-methyl-N-(triphenyl-lambda~5~-phosphanylidene)benzenesulfonamide
• CAS NO: 1058-14-6
• Molecular Formula: C₂₅H₂₂NO₂PS
• Molecular Weight: 431.4864
• Mol File: 1058-14-6.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 590.1°C at 760 mmHg
• Flash Point: 310.7°C
• Density: 1.18g/cm³
• Vapor Pressure: 2.78E-13mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: 4-methyl-N-(triphenylphosphoranylidene)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-N-(triphenylphosphoranylidene)benzenesulfonamide(1058-14-6)
• EPA Substance Registry System: 4-methyl-N-(triphenylphosphoranylidene)benzenesulfonamide(1058-14-6)

Safety Data

• Hazardous Substances Data: 1058-14-6(Hazardous Substances Data)

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 1034-39-5 dibromotriphenylphosphorane 
• 78727-83-0 N-(p-tolylsulfonyl)diphenyltellurimide 
• 603-35-0 triphenylphosphine 
• 71996-32-2 N-(5λ⁴-dibenzo[b,d]thiophen-5-ylidene)-4-methylbenzenesulfonamide 
• 21849-40-1 dibromamine-T 
• 127-65-1 chloroamine-T 
• 64-17-5 ethanol 
• 455-16-3 p-toluenesulfonyl fluoride 
• 242461-31-0 [N-(p-toluenesulfonyl)imino](2-tert-butylsulfonyl)phenyliodinane 
• 76089-77-5 cerium triflate 
• 52093-25-1 europium(III) trifluoromethanesulfonate 
• 1338062-05-7 4-methyl-N-[(2-propoxyphenyl)-λ³-iodanylidene]benzenesulfonamide 
• 941-55-9 4-toluenesulfonyl azide 

Downstream Products

• 135822-90-1 o-chloro-N-tosylbenzaldimine 
• 791-28-6 Triphenylphosphine oxide 
• 146041-79-4 9-(toluene-4-sulfonyl)-9-aza-bicyclo[6.1.0]nonane 
• 148961-16-4 2-hexyl-1-(toluene-4-sulfonyl)-aziridine 
• 116905-62-5 cis-N-tosyl-2-methyl-3-n-propylaziridine 
• 116905-62-5 trans-N-tosyl-2-methyl-3-n-propylaziridine 
• 404345-06-8 1-(toluene-4-sulfonyl)-1-aza-spiro[2.5]octane 
• 147054-74-8 N-(p-toluenesulfonyl)-2,3-diphenylaziridine 
• 17879-98-0 trans-N-(p-toluenesulfonyl)-2,3-diphenylaziridine 
• 137595-22-3 N-(4-tolylsulfonyl)-2-methyl-2-phenylaziridine 
• 24395-14-0 N-(p-tolylsulfonyl)-2-phenylaziridine 
• 97401-87-1 N-tosyl-2-(p-tolyl)aziridine 
• 155721-36-1 2-(4-methoxyphenyl)-1-tosylaziridine 
• 97401-93-9 N-(p-toluenesulfonyl)-2-(4-chlorophenyl)aziridine 

Relevant articles and documents

Facile conversion of hydrazines to iminophosphoranes

-

A Dicopper Nitrenoid by Oxidation of a CuICuICore: Synthesis, Electronic Structure, and Reactivity

A dicopper nitrenoid complex was prepared by formal oxidative addition of the nitrenoid fragment to a dicopper(I) center by reaction with the iminoiodinane PhINTs (Ts = tosylate). This nitrenoid complex, (DPFN)Cu2(μ-NTs)[NTf2]2 (DPFN = 2,7-bis(fluorodi(2-pyridyl)methyl)-1,8-naphthyridine), is a powerful H atom abstractor that reacts with a range of strong C-H bonds to form a mixed-valence Cu(I)/Cu(II) μ-NHTs amido complex in the first example of a clean H atom transfer to a dicopper nitrenoid core. In line with this reactivity, DFT calculations reveal that the nitrenoid is best described as an iminyl (NR radical anion) complex. The nitrenoid was trapped by the addition of water to form a mixed-donor hydroxo/amido dicopper(II) complex, which was independently obtained by reaction of a Cu2(μ-OH)2 complex with an amine through a protonolysis pathway. This mixed-donor complex is an analogue for the proposed intermediate in copper-catalyzed Chan-Evans-Lam coupling, which proceeds via C-X (X = N or O) bond formation. Treatment of the dicopper(II) mixed donor complex with MgPh2(THF)2 resulted in generation of a mixture that includes both phenol and a previously reported dicopper(I) bridging phenyl complex, illustrating that both reduction of dicopper(II) to dicopper(I) and concomitant C-X bond formation are feasible.

Palladium-Catalyzed Stereoselective Hydrodefluorination of Tetrasubstituted gem-Difluoroalkenes

A highly stereoselective palladium(0)-catalyzed hydrodefluorination (HDF) of tetrasubstituted gem-difluoroalkenes is developed. By using catalytic Pd(PPh3)4 (2.5-5 mol percent) and hydrosilane Me2PhSiH, various trisubstituted terminal (E)-monofluoroalkenes can be synthesized with excellent E/Z selectivity (>99:1) and good functional group tolerability. The key stereocontrol should be exerted by an ester-directed C-F bond oxidative addition step in the catalytic cycle.

Designed To React: Terminal Copper Nitrenes and Their Application in Catalytic C?H Aminations

Heteroscorpionate ligands of the bis(pyrazolyl)methane family have been applied in the stabilisation of terminal copper tosyl nitrenes. These species are highly active intermediates in the copper-catalysed direct C?H amination and nitrene transfer. Novel perfluoroalkyl-pyrazolyl- and pyridinyl-containing ligands were synthesized to coordinate to a reactive copper nitrene centre. Four distinct copper tosyl nitrenes were prepared at low temperatures by the reaction with SO2tBuPhINTs and copper(I) acetonitrile complexes. Their stoichiometric reactivity has been elucidated regarding the imination of phosphines and the aziridination of styrenes. The formation and thermal decay of the copper nitrenes were investigated by UV/Vis spectroscopy of the highly coloured species. Additionally, the compounds were studied by cryo-UHR-ESI mass spectrometry and DFT calculations. In addition, a mild catalytic procedure has been developed where the copper nitrene precursors enable the C?H amination of cyclohexane and toluene and the aziridination of styrenes.