115298-63-0

Basic information

• Product Name: (4-METHOXYPHENYL)PHENYLIODONIUM TRIFLATE
• Synonyms: (4-METHOXYPHENYL)PHENYLIODONIUM TRIFLATE
• CAS NO: 115298-63-0
• Molecular Formula: CF₃O₃S*C₁₃H₁₂IO
• Molecular Weight: 460.21
• Mol File: 115298-63-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 109-111 °C
• Appearance: /
• Storage Temp.: Flammables area
• CAS DataBase Reference: (4-METHOXYPHENYL)PHENYLIODONIUM TRIFLATE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-METHOXYPHENYL)PHENYLIODONIUM TRIFLATE(115298-63-0)
• EPA Substance Registry System: (4-METHOXYPHENYL)PHENYLIODONIUM TRIFLATE(115298-63-0)

Safety Data

• Hazard Codes: Xn-F
• Statements: 44-36/37/38-20/21/22-11
• Safety Statements: 36/37/39-26-16
• Hazardous Substances Data: 115298-63-0(Hazardous Substances Data)

Usage

Chemical Properties

off-white to greyish-beige crystalline powder

Upstream product

• 1493-13-6 trifluorormethanesulfonic acid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 100-66-3 methoxybenzene 
• 536-80-1 iodosylbenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 588-96-5 4-bromoethoxybenzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 27126-77-8 (4-methoxyphenyl)phenyliodonium p-toluenesulfonate 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 4336-16-7 C₂H₃O₂^(1-)*C₁₃H₁₂IO⁽¹⁺⁾ 
• 71-43-2 benzene 
• 696-62-8 para-iodoanisole 
• 591-50-4 iodobenzene 

Downstream Products

• 74610-81-4 methyl-(4-methoxyphenyl)-propanedioic acid ethyl diester 
• 34009-61-5 diethyl 2-methyl-2-phenylmalonate 
• 1655-68-1 1-methoxy-3-phenoxybenzene 
• 58005-59-7 4-methyl-3'-methoxy-diphenyl ether 
• 3661-49-2 3-methoxy-N-(4-methoxyphenyl)benzenamine 
• 101-16-6 3-methoxy-N-phenylaniline 
• 519-87-9 N,N-diphenylacetamide 
• 124244-39-9 2-phenyl-2,5-dihydrofuran 
• 84132-74-1 2-(4-methoxyphenyl)-2,5-dihydrofuran 
• 70974-10-6 5,5-dimethyl-3-phenylimidazolidine-2,4-dione 
• 92668-55-8 3-(4-methoxyphenyl)-5,5-dimethylimidazolidine-2,4-dione 
• 557780-43-5 4-methoxy-N-morpholinobenzenesulfonamide 
• 351186-42-0 N‐morpholinobenzenesulfonamide 
• 100-17-4 para-methoxynitrobenzene 

Relevant articles and documents

New synthesis of diaryliodonium sulfonates from arylboronic acids

Diaryliodonium salts, precursors to [18F]fluoroaromatics, have been prepared, in a regioselective manner, from readily available arylboronic acids eliminating the need for acid sensitive and toxic organotin intermediates. (C) 2000 Elsevier Science Ltd.

Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts

A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.

One-Pot C?H Functionalization of Arenes by Diaryliodonium Salts

A transition-metal-free, mild, and highly regioselective synthesis of nitroarenes from arenes has been developed. The products are obtained in a sequential one-pot reaction by nitration of iodine(III) reagents with two carbon ligands, which are formed in situ from iodine(I). This novel concept has been extended to formation of aryl azides, and constitutes an important step towards catalytic reactions with these hypervalent iodine reagents. An efficient nitration of isolated diaryliodonium salts has also been developed, and the mechanism is proposed to proceed by a [2,2] ligand coupling pathway.

Arylation with unsymmetrical diaryliodonium salts: A chemoselectivity study

Phenols, anilines, and malonates have been arylated under metal-free conditions with twelve aryl(phenyl)iodonium salts in a systematic chemoselectivity study. A new "anti-ortho effect" has been identified in the arylation of malonates. Several "dummy groups" have been found that give complete chemoselectivity in the transfer of the phenyl moiety, irrespective of the nucleophile. An aryl exchange in the diaryliodonium salts has been observed under certain arylation conditions. DFT calculations have been performed to investigate the reaction mechanism and to elucidate the origins of the observed selectivities. These results are expected to facilitate the design of chiral diaryliodonium salts and the development of catalytic arylation reactions that are based on these sustainable and metal-free reagents. Copyright