1204518-08-0

Basic information

• Product Name: [3-(TrifluoroMethyl)phenyl](2,4,6-triMethylphenyl)iodoniuM triflate
• Synonyms: [3-(TrifluoroMethyl)phenyl](2,4,6-triMethylphenyl)iodoniuM triflate;[3-(Trifluoromethyl)phenyl](2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate;mesityl(3-(trifluoromethyl)phenyl)iodonium;Iodonium, [3-(trifluoromethyl)phenyl](2,4,6-trimethylphenyl)-, 1,1,1-trifluoromethanesulfonate (1:1)
• CAS NO: 1204518-08-0
• Molecular Formula: CF₃O₃S*C₁₆H₁₅F₃I
• Molecular Weight: 540.2590892
• Mol File: 1204518-08-0.mol

Chemical Properties

• Melting Point: 183°C(lit.)
• Appearance: /
• Solubility: soluble in Methanol
• BRN: 20040214
• CAS DataBase Reference: [3-(TrifluoroMethyl)phenyl](2,4,6-triMethylphenyl)iodoniuM triflate(CAS DataBase Reference)
• NIST Chemistry Reference: [3-(TrifluoroMethyl)phenyl](2,4,6-triMethylphenyl)iodoniuM triflate(1204518-08-0)
• EPA Substance Registry System: [3-(TrifluoroMethyl)phenyl](2,4,6-triMethylphenyl)iodoniuM triflate(1204518-08-0)

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: 1204518-08-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
[3-(TrifluoroMethyl)phenyl](2,4,6-triMethylphenyl)iodoniuM triflate is used as a reagent for meta-selective copper-catalyzed C-H bond arylation. This application is significant because it allows for the selective formation of aryl-aryl bonds at the meta position, which is crucial for the synthesis of specific organic compounds with desired structural features. The use of this reagent in copper-catalyzed reactions enables chemists to achieve high levels of selectivity and efficiency, leading to the production of target molecules with minimal side reactions or byproducts.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, [3-(TrifluoroMethyl)phenyl](2,4,6-triMethylphenyl)iodoniuM triflate may be employed as a key intermediate in the synthesis of various drug candidates. Its unique structural features and reactivity make it a valuable building block for the development of new medications with improved pharmacological properties. By utilizing this reagent in the synthesis process, researchers can potentially create novel drugs with enhanced efficacy, selectivity, and reduced side effects.
Used in Material Science:
[3-(TrifluoroMethyl)phenyl](2,4,6-triMethylphenyl)iodoniuM triflate can also be used in the field of material science, particularly in the development of advanced materials with specific properties. Its unique structure and reactivity can be exploited to synthesize novel polymers, coatings, and other materials with tailored characteristics, such as improved thermal stability, chemical resistance, or electrical conductivity. These materials can find applications in various industries, including electronics, aerospace, and automotive.

Upstream product

• 1493-13-6 trifluorormethanesulfonic acid 
• 401-81-0 m-trifluoromethylphenyl iodide 
• 108-67-8 1,3,5-trimethyl-benzene 

Downstream Products

• 1330681-49-6 (R)-3-(2-(3-(trifluoromethyl)phenyl)propanoyl)oxazolidin-2-one 
• 1449689-65-9 4-(4-methoxyphenyl)-3-(3-(trifluoromethyl)phenyl)-1,2-dihydronaphthalene 
• 1618681-43-8 (3-trifluoromethylphenyl)(mesityl)iodonium hexafluorophosphate(V) 
• 38726-06-6 O,O-diethyl S-(3-(trifluoromethyl)phenyl)phosphorothioate 
• 54057-97-5 diethyl <3-(trifluoromethyl)phenyl>phosphonate 
• 98-17-9 3-Trifluoromethylphenol 
• 167933-07-5 flibanserin 

Relevant articles and documents

One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone-sulfuric acid

A facile synthesis of diaryliodonium salts utilizing Oxone as versatile and cheap oxidant has been developed. This method shows wide applicability and can be used for the preparation of iodonium salts containing electron-donating or electron-withdrawing groups in good yields. In addition, this procedure can be applied to the preparation of symmetric iodonium salts directly from arenes via a one-pot iodination-oxidation sequence.

Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts

Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3H)-ones and 1,2,4-oxadiazole-5-thiol. (Figure presented.).

Catalyst-Free Arylation of Tertiary Phosphines with Diaryliodonium Salts Enabled by Visible Light

The visible-light-induced arylation of tertiary phosphines with aryl(mesityl)iodonium triflates to produce the quaternary phosphonium salts occurs under mild, metal, and catalyst-free conditions. Photo-excited EDA complexes between diaryliodonium salts an

Glycosyl Cross-Coupling with Diaryliodonium Salts: Access to Aryl C -Glycosides of Biomedical Relevance

A stereospecific cross-coupling reaction of anomeric nucleophiles with diaryliodonium triflates resulting in the synthesis of aryl C-glycosides is reported. This process capitalizes on a stereoretentive reaction of configurationally stable C1 stannanes and is promoted by a palladium catalyst in the presence of a bulky phosphine ligand that suppresses the undesired β-elimination. The utility of this reaction has been demonstrated in the preparation of a series of C-glycosides derived from common saccharides resulting in exclusive transfer of anomeric configuration from the anomeric nucleophile to the product, and in the synthesis of empagliflozin, a commercial antidiabetic drug.

N-Arylation of DABCO with Diaryliodonium Salts: General Synthesis of N-Aryl-DABCO Salts as Precursors for 1,4-Disubstituted Piperazines

Employing DABCO as a substrate, aryl(mesityl)iodonium triflates are introduced as arylating agents for a tertiary sp3-nitrogen. Mild conditions and exceptional selectivity of the aryl group transfer allow unprecedented N-aryl-DABCO salts to be obtained, bearing substituents of different electronic natures. This metal-free methodology has no analogy among known transition-metal-based reactions. The utility of isolated N-aryl-DABCO salts is demonstrated for the preparation of flibanserin.

Facile One-Pot Synthesis of Diaryliodonium Salts from Arenes and Aryl Iodides with Oxone

A straightforward synthesis of diaryliodonium salts is achieved by using Oxone as the stoichiometric oxidant. Slow addition is the key to obtaining good yields and purities of the reaction products, which are highly useful reagents in many different areas of organic synthesis.

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.

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).

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.