887144-94-7 | 1-(Trifluoromethyl)-1,2-benziodoxol-3(1H)-one

CAS:887144-94-7 | 1-(Trifluoromethyl)-1,2-benziodoxol-3(1H)-one ,Description

1-(Trifluoromethyl)-1,2-benziodoxol-3(1H)-one, also known as 1-trifluoromethylbenziodoxolone (TFB), is an organic compound belonging to the family of benziodoxolones. It is a colorless, odorless, and crystalline solid that is soluble in water, alcohols, and other organic solvents. TFB is widely used in scientific research due to its unique properties such as its high solubility, low toxicity, and low volatility.
 

Scientific Research Applications

Reactivity with THF and Formation of Trifluoromethyl Ethers

1-(Trifluoromethyl)-1,2-benziodoxol-3(1H)-one demonstrates the ability to transfer the electrophilic CF3 group to the oxygen atom of tetrahydrofuran (THF), leading to a new ring-opening reaction and the production of trifluoromethyl ethers. This discovery provides insight into the mechanism of action of this reagent in organic synthesis (Fantasia, Welch, & Togni, 2010).

Trifluoromethylation of Sulfonic Acids

It is used for trifluoromethylating various sulfonic acids under mild conditions, offering good to excellent yields. This reaction shows clean second-order kinetics with minimal substrate electronic effects (Koller, Huchet, Battaglia, Welch, & Togni, 2009).

Preparation of Organosulfonyloxy Derivatives

Organosulfonyloxy derivatives of 1,2-benziodoxol-3(1H)-one can be prepared in high yield by reacting 1-hydroxybenziodoxoles with corresponding sulfonic acids. This method produces stable, microcrystalline solids suitable for various synthetic applications (Zhdankin, Kuehl, Krasutsky, Bolz, & Simonsen, 1996).

Electrophilic Trifluoromethylation in Catalysis

Methyltrioxorhenium acts as a catalyst for the direct electrophilic trifluoromethylation of aromatic and heteroaromatic compounds using 1-(trifluoromethyl)-1,2-benziodoxol-3(1H)-one. This process involves radical species and can be carried out in chloroform solvent at 70 °C (Mejía & Togni, 2012) .

Gold-Catalysed Oxyarylation of Olefins

1-Hydroxy-1,2-benziodoxol-3(1H)-one is an effective terminal oxidant for gold-catalyzed, three-component oxyarylation reactions. It broadens the scope of oxyarylation to include styrenes and gem-disubstituted olefins, expanding the range of substrates in this domain (Ball, Lloyd‐Jones, & Russell, 2012).

Role in the Synthesis of Dess-Martin Periodinane

1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide plays a crucial role in the synthesis of Dess-Martin periodinane. Its physical form affects the reproducibility of converting it to I-triacetoxy derivative, demonstrating its significance in organic chemistry (Stevenson, Treacy, & Nieuwenhuyzen, 1997).

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