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Usage

Uses

Used in Organic Synthesis:
(4-bromomethylphenyl)(2’,4’,6’-trimethoxyphenyl)iodonium tosylate is used as a reagent for the transfer of the benzyl group to various nucleophiles. This property makes it a versatile component in the synthesis of arylmethanes and aryl ethers through benzyl group transfer reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (4-bromomethylphenyl)(2’,4’,6’-trimethoxyphenyl)iodonium tosylate is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to transfer the benzyl group allows for the creation of complex organic molecules with potential therapeutic applications.
Used in Chemical Research:
(4-bromomethylphenyl)(2’,4’,6’-trimethoxyphenyl)iodonium tosylate is also used in chemical research as a model compound to study the reactivity and properties of iodonium and tosylate groups. This helps in understanding the underlying mechanisms of various chemical reactions and contributes to the advancement of organic chemistry.

Upstream product

• 104-15-4 toluene-4-sulfonic acid 
• 41018-45-5 naphthalen-1-yl-λ³-iodanediyl diacetate 
• 100-66-3 methoxybenzene 
• 90-14-2 1-Iodonaphthalene 
• 621-23-8 1,2,3-trimethoxybenzene 
• 16004-15-2 1-bromomethyl-4-iodobenzene 

Downstream Products

• 134430-70-9 p-[18F]fluorobenzyl bromide 

Relevant academic research and scientific papers

Unsymmetrical Aryl(2,4,6-trimethoxyphenyl)iodonium Salts: One-Pot Synthesis, Scope, Stability, and Synthetic Studies

Diaryliodonium salts have recently attracted significant attention as metal-free-arylation reagents in organic synthesis, and efficient access to these salts is critical for advancement of their use in reaction discovery and development. The trimethoxybenzene-derived auxiliary is a promising component of unsymmetrical variants, yet access remains limited. Here, a one-pot synthesis of aryl(2,4,6-trimethoxyphenyl)iodonium salts from aryl iodides, m-CPBA, p-toluenesulfonic acid, and trimethoxybenzene is described. Optimization of the reaction conditions for this one-pot synthesis was enabled by the method of multivariate analysis. The reaction is fast (85% average), and has broad substrate scope (>25 examples) including elaborate aryl iodides. The utility of these reagents is demonstrated in moderate to high yielding arylation reactions with C-, N-, O-, and S-nucleophiles including the synthesis of a liquid crystal molecule.

Single-step syntheses of no-carrier-added functionalized [ 18F]fluoroarenes as labeling synthons from diaryliodonium salts

Radiotracers labelled with short-lived fluorine-18 (t1/2 = 109.7 min) are keenly sought for biomedical imaging with positron emission tomography (PET). The radiotracers are mostly required at high specific radioactivities, necessitating their radiosyntheses from cyclotron-produced no-carrier-added [18F]fluoride ion. PET radiotracers encompass wide structural diversity and molecular weight. Hence, diverse 18F-labeling methodology is needed to accomplish the required radiosyntheses in a simple and rapid manner. A useful strategy is to introduce nucleophilic [ 18F]fluoride ion first into a labeling synthon that may then be applied to label the target radiotracer. Here, we show that various functionalized [18F]fluoroarenes may be rapidly synthesized as labeling synthons through single-step reactions of appropriate diaryliodonium salts with [18F]fluoride ion. Decay-corrected radiochemical yields (RCYs) varied with position of functional group, choice of electron-rich aryl ring in the diaryliodonium salt, and choice of anion. Under best conditions, 18F-labeled fluorobenzaldehydes, fluorobenzyl halides, fluorobenzoic acid esters and fluorophenyl ketones were obtained selectively in 40-73%, 20-55%, 46-89% and 81-98% RCYs, respectively. This versatile straightforward methodology will enhance the scope for producing structurally complex, yet useful, PET radiotracers.