17763-91-6 | CATECHOL BIS(TRIFLUOROMETHANESULFONATE)

CAS:17763-91-6 | CATECHOL BIS(TRIFLUOROMETHANESULFONATE),Description

Catechol bis(trifluoromethanesulfonate) is a compound that is not directly mentioned in the provided papers, but its related chemistry can be inferred from the studies involving trifluoromethanesulfonate derivatives and related sulfur-nitrogen compounds. Trifluoromethanesulfonate, often referred to as triflate, is a functional group known for its utility in various organic synthesis reactions due to its strong electron-withdrawing properties and ability to stabilize reaction intermediates.

Synthesis Analysis

The synthesis of trifluoromethanesulfonate derivatives is highlighted in several studies. For instance, a solvent-free bisindolylation reaction of indoles with alkyl and aryl trifluoromethyl ketones was catalyzed by trifluoromethanesulfonic acid, leading to the formation of trifluoromethyl-substituted bisindolylalkane derivatives. Additionally, bismuth(III) trifluoromethanesulfonate has been used as an efficient catalyst for the sulfonylation of arenes, demonstrating the versatility of trifluoromethanesulfonate in facilitating electrophilic aromatic substitutions.

Molecular Structure Analysis

The molecular structure of bis(trifluoromethyl)sulfonyl)amine, a related compound, has been analyzed, revealing extensive electron delocalization from planar, sp2-hybridized nitrogen into 3d orbitals of sulfur. This delocalization results in a shortening of the S-N bond upon deprotonation, which is a characteristic that could be relevant to the behavior of catechol bis(trifluoromethanesulfonate) as well.

Chemical Reactions Analysis

Trifluoromethanesulfonate derivatives are involved in various chemical reactions. Bismuth(III) trifluoromethanesulfonate has been shown to catalyze the allylation of dioxolanes, leading to the formation of highly functionalized esters. Moreover, strong Brønsted acids like bis(trifluoromethanesulfon)imide have been used to catalyze hetero-Michael addition reactions with superior scope, reaction rates, and yields compared to Lewis acid-catalyzed processes.

Physical and Chemical Properties Analysis

The physical and chemical properties of trifluoromethanesulfonate derivatives are influenced by their strong electron-withdrawing trifluoromethyl groups. These properties are crucial for their reactivity and stability in various organic reactions. For example, scandium(III) trifluoromethanesulfonate has been used as a mild and environmentally friendly catalyst in the synthesis of bis(3'-indolyl)alkanes and bis(3'-indolyl)-1-deoxyalditols, indicating the potential for trifluoromethanesulfonate derivatives to be used in green chemistry applications.

Scientific Research Applications

• Catalysis in Organic Reactions

  Bis(trifluoromethanesulfon)imide, a compound related to catechol bis(trifluoromethanesulfonate), has been used as a catalyst in the hetero-Michael addition of nitrogen, oxygen, and sulfur nucleophiles to unsaturated ketones and other substrates, showing superior scope, reaction rates, and yields compared to Lewis acid-catalyzed processes (Wabnitz & Spencer, 2003) .

• Synthesis of Fluorinated Compounds

  Trifluoromethanesulfonic acid, a closely related compound, has been used to synthesize fluorinated bisphenols and tetraphenols through a condensation reaction with catechol and other bisphenols, yielding good results (Tao et al., 2013).

• Ionic Liquid Research

  Studies have explored the properties of ionic liquids containing bis(trifluoromethyl)sulfonyl imide and trifluoromethanesulfonate anions, useful in applications such as electrolytes in batteries and other electrochemical devices (Gouveia et al., 2017).

• Cross-Coupling Reactions

  Aryl and heteroaryl bis(catechol) silicates, undergoing palladium-catalyzed cross-coupling with aryl triflates, have shown excellent yields. These bis(catechol) silicates are stable and prepared from catechol and an aryl siloxane (Seganish & DeShong, 2004).

• Electrophilic Acylation Catalyst

  Bis(trifluoroalkylsulfonylimino)trifluoromethanesulfonic acid has been used as a catalyst in the Friedel–Crafts acylation of aromatic substrates (Posternak et al., 2009) .

• Synthesis of Palladium Complexes

  Palladium bis(trifluoromethanesulfonate) has been synthesized for use in the preparation of palladium(II) complexes, showcasing its utility in inorganic and coordination chemistry (Murata & Ido, 1994).

• Structure and Vibrational Frequencies Studies

  Ab initio studies of bis(trifluoromethanesulfone)imide ion pairs have been conducted to understand their structure and vibrational frequencies, important for applications in materials science and chemistry (Gejji et al., 1999).

• Ionic Conductivity in Polymer Electrolytes

  Studies on the ionic conductivity of polymer electrolytes doped with salts of trifluoromethanesulfonate and bis(trifluoromethanesulfonyl)imidate have been conducted, relevant for battery technology and material sciences (Lee & Allcock, 2010).

Safety And Hazards

Catechol bis(trifluoromethanesulfonate) is classified as a dangerous substance. It can cause severe skin burns and eye damage, and may be corrosive to metals. Safety precautions include avoiding breathing dusts or mists, wearing protective clothing, and storing in a corrosive resistant container.

Future Directions

While specific future directions for Catechol bis(trifluoromethanesulfonate) are not mentioned in the search results, it is noted that understanding and controlling the redox activity and chemical reactivity of catechols is essential for developing new bioadhesive underwater glues.

More Information