210823-54-4

Basic information

• Product Name: (2-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate
• Synonyms: (2-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate;(2-Methylphenyl)(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate;Mesityl(o-tolyl)iodonium triflate;Iodonium, (2-methylphenyl)(2,4,6-trimethylphenyl)-, 1,1,1-trifluoromethanesulfonate (1:1)
• CAS NO: 210823-54-4
• Molecular Formula: C17H18F3IO3S
• Molecular Weight: 486.2876996
• Mol File: 210823-54-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 166.0 to 170.0 °C
• Appearance: /
• Solubility: soluble in Methanol
• BRN: 7965987
• CAS DataBase Reference: (2-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate(CAS DataBase Reference)
• NIST Chemistry Reference: (2-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate(210823-54-4)
• EPA Substance Registry System: (2-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate(210823-54-4)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 210823-54-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(2-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate is used as a source of electrophilic methyl and aryl cations in organic synthesis reactions. Its ability to generate these cations allows for the formation of new carbon-carbon and carbon-heteroatom bonds, facilitating the synthesis of a wide range of organic compounds.
Used as a Mild Oxidizing Agent:
In various chemical transformations, (2-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate serves as a mild oxidizing agent. Its oxidizing properties enable the conversion of certain functional groups into more reactive or stable forms, broadening the scope of possible reactions and products.
Used in the Generation of Other Iodonium Compounds:
(2-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate can act as a precursor for the synthesis of other iodonium compounds. These derived compounds exhibit diverse applications in organic chemistry, including as catalysts, reagents, or intermediates in complex organic transformations.
Used in Chemical Research and Industry:
Due to its unique structure and reactivity, (2-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate is an important tool in chemical research and industry. It aids in the development of new synthetic methods, the discovery of novel chemical reactions, and the optimization of existing processes, contributing to advancements in the field of organic chemistry.

Upstream product

• 615-37-2 ortho-methylphenyl iodide 
• 1493-13-6 trifluorormethanesulfonic acid 
• 108-67-8 1,3,5-trimethyl-benzene 

Downstream Products

• 5033-67-0 2-(2-methylphenyl)-1-phenyl-1-ethanone 
• 59960-38-2 2-phenyl-N-(o-tolyl)propanamide 
• 1449307-68-9 2-methyl-6-(4-methylpyridin-1-ium-1-yl)phenolate 

Relevant articles and documents

Versatile and base-free copper-catalyzed α-arylations of aromatic ketones using diaryliodonium salts

A ligand and base-free copper catalyzed synthetic method for the efficient α-arylation of aromatic ketones is described. In order to avoid strong bases, ketone-derived silyl enol ethers were employed. Their reaction with diaryliodonium salts as aryl source provided the intermolecular C–C coupling displaying good functional group tolerance and requiring low catalyst loading.

Visible Light Accelerated Vinyl C–H Arylation in Pd-Catalysis: Application in the Synthesis of ortho Tetra-substituted Vinylarene Atropisomers

A visible light accelerated C–H functionalization reaction in palladium-catalyzed arylation of vinyl arenes with diaryliodonium salts is reported in the absence of additional photosensitizer. The kinetic isotope effect (kH/kD) was ch

Flow Synthesis of Diaryliodonium Triflates

A safe and scalable synthesis of diaryliodonium triflates was achieved using a practical continuous-flow design. A wide array of electron-rich to electron-deficient arenes could readily be transformed to their respective diaryliodonium salts on a gram scale, with residence times varying from 2 to 60 s (44 examples).

A Modular Flow Design for the meta-Selective C?H Arylation of Anilines

Described herein is an effective and practical modular flow design for the meta-selective C?H arylation of anilines. The design consists of four continuous-flow modules (i.e., diaryliodonium salt synthesis, meta-selective C?H arylation, inline copper extraction, and aniline deprotection) which can be operated either individually or consecutively to provide direct access to meta-arylated anilines. With a total residence time of 1 hour, the desired product could be obtained in high yield and excellent purity without the need for column chromatography, and the residual copper content meets the standards for parenterally administered pharmaceutical substances.

A Modular Synthesis of 4-Aminoquinolines and [1,3] N-to-C Rearrangement to Quinolin-4-ylmethanesulfonamides

A copper-catalyzed regiocontrolled three-component reaction afforded diversified 4-aminoquinolines using nitriles, diaryliodoniums, and ynamides. The C7-substituted regioisomers were formed regioselectively when meta-substituted phenyliodonium salts were used. [1,3] N-to-C rearrangement of the products to quinolin-4-ylmethanesulfonamides and simultaneous deprotection of benzyl and sulfonamide group were newly developed. Finally, antimalarial CK-2-68 was successfully prepared.

Copper-catalyzed oxidative ring closure of ortho-cyanoanilides with hypervalent iodonium salts: Arylation-ring closure approach to iminobenzoxazines

A novel, highly modular synthetic methodology with high functional group tolerance was developed for the construction of iminobenzoxazine derivatives from ortho-cyanoanilides and diaryliodonium triflates via an oxidative arylation-cyclization path. The reaction is supposed to involve the formation of highly active aryl-copper(III) species. In this novel transformation, copper(II) triflate was used as catalyst in 1,2-dichloroethane or ethyl acetate and the reaction takes place at 75 °C in 2-16 h.

Transition-Metal-Free N-Arylation of Pyrazoles with Diaryliodonium Salts

A new synthetic method was developed for the N-arylation of pyrazoles using diaryliodonium salts. The transformation does not require any transition-metal catalyst and provides the desired N-arylpyrazoles rapidly under mild reaction condition in the presence of aqueous ammonia solution as a mild base without the use of inert atmosphere. The chemoselectivity of unsymmetric diaryliodonium salts was also explored with large number of examples.

Utilization of Copper-Catalyzed Carboarylation-Ring Closure for the Synthesis of New Oxazoline Derivatives

A copper-catalyzed carboarylation-ring-closure strategy was used for the modular synthesis of oxazolines via the reaction of 1-aryl- and 1-alkylpropargylamides and diaryliodonium salts. The novel approach enables the efficient, modular synthesis of oxazol

Copper-catalyzed oxidative ring closure and carboarylation of 2-ethynylanilides

A new copper-catalyzed oxidative ring closure of ethynyl anilides with diaryliodonium salts was developed for the highly modular construction of benzoxazines bearing a fully substituted exo double bond. The oxidative transformation includes an unusual 6-exo-dig cyclization step with the formation of C-O and C-C bonds.

Enantioselective α-arylation of N-acyloxazolidinones with copper(II)-bisoxazoline catalysts and diaryliodonium salts

A new strategy for the catalytic enantioselective α-arylation of N-acyloxazolidinones with chiral copper(II)-bisoxazoline complexes and diaryliodonium salts is described. The mild catalytic conditions are operationally simple, produce valuable synthetic building blocks in excellent yields and enantioselectivities, and can be applied to the synthesis of important nonsteroidal anti-inflammatory agents and their analogues.