1204518-02-4

Basic information

• Product Name: (4-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate
• Synonyms: (4-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate;(4-Methylphenyl)(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate;Mesityl(p-tolyl)iodonium triflate
• CAS NO: 1204518-02-4
• Molecular Formula: CF₃O₃S*C₁₆H₁₈I
• Molecular Weight: 486.2876996
• Mol File: 1204518-02-4.mol
• Article Data: 21

Chemical Properties

• Melting Point: 177.0 to 182.0 °C
• Appearance: /
• Solubility: soluble in Methanol
• BRN: 20040208
• CAS DataBase Reference: (4-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate(CAS DataBase Reference)
• NIST Chemistry Reference: (4-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate(1204518-02-4)
• EPA Substance Registry System: (4-Methylphenyl)(2,4,6-triMethylphenyl)iodoniuM triflate(1204518-02-4)

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: 1204518-02-4(Hazardous Substances Data)

Usage

Uses

(4-Methylphenyl)(2,4,6-trimethylphenyl)iodonium Triflate is a reagent used in organic synhesis, normally applied in arylation reactions and in iodonium metathesis reactions.

Upstream product

• 1493-13-6 trifluorormethanesulfonic acid 
• 624-31-7 4-tolyl iodide 
• 108-67-8 1,3,5-trimethyl-benzene 
• 33035-41-5 2-(diacetoxyiodo)mesitylene 
• 108-88-3 toluene 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 

Downstream Products

• 1319735-29-9 11-[1-p-tolylbut-(Z)-ylidene]-6,11-dihydroindolo[1,2-b]isoquinoline 
• 99495-15-5 3-(p-tolyl)cyclohexan-1-one 

Relevant articles and documents

Practical synthesis of diaryliodonium(iii) triflates using ArI(OAc)2/TfOH/MeCN reaction system

Diaryliodonium(iii) triflates were synthesized in a safe manner by the reaction of aryliodine(iii) diacetates ArI(OAc)2 with triflic acid (TfOH) in MeCN under mild exothermic conditions. This method provides access to a variety of diaryliodoniu

Synthesis of Diverse Aryliodine(III) Reagents by Anodic Oxidation?

An anodic oxidation enabled synthesis of hypervalent iodine(III) reagents from aryl iodides is demonstrated. Under mild electrochemical conditions, a range of aryliodine(III) reagents including iodosylarenes, (difunctionaliodo)arenes, benziodoxoles and diaryliodonium salts can be efficiently synthesized and derivatized in good to excellent yields with high selectivity. As only electrons serve as the oxidation reagents, this method offers a more straightforward and sustainable manner avoiding the use of expensive or hazardous chemical oxidants.

Recyclable synthesis of mesityl iodonium(III) salts

An efficient protocol for C–H condensation of hypervalent iodine compounds toward arenes in fluoroalcohols has been applied to the recyclable preparation of mesityl iodonium(III) salts. The electrophilicities of [hydroxy(tosyloxy)iodo]mesitylene (MesI(OH)OTs) and iodomesitylene diacetate (MesI(OAc)2) are suitably enhanced in 2,2,2-trifluoroethanol. A series of nucleophilic aromatic compounds react smoothly with MesI(OH)OTs and MesI(OAc)2 or in situ hypervalent iodine(III) species, generated from iodomesitylene, to provide the target mesityl iodonium(III) salts in good yields at room temperature with broad functional group tolerance. This C–H condensation strategy merits high para-regioselectivities during the diaryliodonium(III) salt formation, but the major limitation in the case of low-reactive aromatic substrates is byproduct formation resulting from the self-condensation of the nucleophilic mesitylene ring in MesI(OH)OTs and MesI(OAc)2.