Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate
[CAS# 147531-11-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonate / sulfinate
• Name: Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate
• Molecular Formula: C₁₄H₁₀F₆O₃S₂
• Molecular Weight: 404.35
• CAS Registry Number: 147531-11-1
• EC Number: 809-133-6
• SMILES: C1=CC=C(C=C1)[S+](C2=CC=CC=C2)C(F)(F)F.C(F)(F)(F)S(=O)(=O)[O-]

Properties

• Melting point: 84-85 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate, often abbreviated as DPTS, is a sulfonium salt notable for its applications in organic synthesis and materials science. With the molecular formula C13H10F6O3S2, this compound serves as a potent electrophilic reagent, particularly valuable in the field of fluorinated compounds.

The discovery of DPTS can be traced back to advancements in the synthesis of organofluorine compounds, which have gained significant attention due to their unique properties and widespread applications. The incorporation of trifluoromethyl groups into organic molecules enhances their chemical stability, lipophilicity, and biological activity, making them essential in pharmaceuticals and agrochemicals. Researchers aimed to develop effective reagents that could introduce trifluoromethyl groups into various substrates, leading to the exploration of sulfonium salts like DPTS.

One of the primary applications of diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate lies in its role as a trifluoromethylating agent. It facilitates the introduction of trifluoromethyl groups into organic substrates, allowing chemists to modify the properties of molecules for specific applications. The use of DPTS in trifluoromethylation reactions has enabled the development of a range of functionalized compounds, which are critical in drug discovery and development. The ability to synthesize compounds with enhanced biological activity can lead to the identification of new therapeutic agents for various diseases.

In addition to its use in organic synthesis, DPTS finds applications in materials science. The incorporation of trifluoromethyl groups into polymers and materials often results in enhanced thermal stability, chemical resistance, and hydrophobic properties. This makes DPTS a valuable reagent for the synthesis of advanced materials, including coatings and adhesives, which require specific physical properties. Researchers are investigating the use of DPTS in the preparation of high-performance polymers that can withstand harsh environments while maintaining their integrity.

Furthermore, diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate is also utilized in photochemical reactions. Upon irradiation, it can undergo homolytic cleavage, generating reactive trifluoromethyl radicals. These radicals can participate in a variety of subsequent reactions, expanding the utility of DPTS in radical chemistry. This capability makes DPTS an important tool for chemists seeking to explore new reaction pathways and develop innovative synthetic methodologies.

In summary, diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate is a versatile reagent with significant applications in organic synthesis and materials science. Its ability to introduce trifluoromethyl groups into organic substrates has made it a valuable asset in drug discovery and the development of advanced materials. As research continues, the potential applications of DPTS are likely to expand, further emphasizing its importance in modern chemistry.