887144-97-0 | 3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole

CAS:887144-97-0 | 3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole ,Description

3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole (DMTB) is a heterocyclic compound with a molecular formula of C9H7F3O2. It is a colorless to light yellow solid with a melting point of 116–117 °C and a boiling point of 225–226 °C. DMTB is a versatile starting material for the synthesis of heterocyclic compounds, such as quinolines, pyridines, and thiophenes. It is also a useful reagent for the preparation of various fluorinated compounds. 
 

Scientific Research Applications

Synthesis and Reactivity

• Organosulfonyloxy Derivatives Preparation: 3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole derivatives have been synthesized, showing potential in the preparation of various organosulfonyloxy derivatives. This process involves reactions with sulfonic acids and alkynyltrimethylsilanes, demonstrating a pathway to diverse chemical structures (Zhdankin et al., 1996).

Electrophilic Trifluoromethylation

• Trifluoromethylation of Hydrogen Phosphates: The compound has been used in the trifluoromethylation of hydrogen phosphates, a process important in developing novel compounds with potential applications in various fields (Santschi, Geissbühler & Togni, 2012).
• Trifluoromethyl Transfer Agent: It serves as a trifluoromethyl transfer agent, a crucial function in synthesizing trifluoromethylated compounds, which are increasingly significant in materials science and pharmaceuticals (Eisenberger et al., 2012).

Chemical Reactions and Mechanisms

• Arenes and N-heteroarenes Trifluoromethylation: This compound facilitates the trifluoromethylation of arenes and N-heteroarenes, expanding the range of compounds that can be synthesized using this method (Wiehn, Vinogradova & Togni, 2010).
• Electron Density and Reactivity Analysis: Insights into the electron density and reactivity of the compound have been gained, revealing the importance of the σ hole on the hypervalent iodine atom for adduct formation (Wang, Kalf & Englert, 2018).

Novel Applications and Studies

• S-Hydrogen Phosphorothioates Trifluoromethylation: The compound has been used to convert S-hydrogen phosphorothioates to their S-trifluoromethyl derivatives, revealing interesting aspects of the reaction's kinetics and mechanisms (Santschi & Togni, 2011).
• Expanding Hypervalent Iodine Reagents Scope: New hypervalent iodine reagents based on the 3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole scaffold have been explored, showing potential for various synthetic applications, including in chemical biology (Matoušek et al., 2016) .

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