2,4-Dihydroxyphenyldimethylsulfonium triflate
[CAS# 180787-54-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonate / sulfinate
• Name: 2,4-Dihydroxyphenyldimethylsulfonium triflate
• Synonyms: Dimethyl-2,4-dihydroxyphenylsulfonium triflate
• Molecular Formula: C₈H₁₁O₂S^.CF₃O₃S
• Molecular Weight: 320.31
• CAS Registry Number: 180787-54-6
• SMILES: C[S+](C)C1=C(C=C(C=C1)O)O.C(F)(F)(F)S(=O)(=O)[O-]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

2,4-Dihydroxyphenyldimethylsulfonium triflate is a specialized chemical compound that has garnered interest in the field of organic synthesis and catalysis. This compound, which features a sulfonium cation paired with the triflate anion, was synthesized as part of ongoing research to develop efficient catalysts for various organic reactions. Its unique structure, characterized by two hydroxyl groups on a phenyl ring, offers a combination of reactivity and stability, making it suitable for a range of applications in synthetic chemistry.

The discovery of 2,4-dihydroxyphenyldimethylsulfonium triflate emerged from efforts to create new sulfonium salts with improved catalytic properties. Researchers aimed to design compounds that could facilitate nucleophilic substitutions and other reactions more efficiently than conventional catalysts. The introduction of hydroxyl groups on the phenyl ring not only enhances the compound's solubility in polar solvents but also increases its ability to stabilize reaction intermediates, thus improving reaction rates and yields.

One of the primary applications of 2,4-dihydroxyphenyldimethylsulfonium triflate is in the field of organic synthesis, where it serves as a highly effective electrophilic reagent. Its ability to activate substrates toward nucleophilic attack makes it particularly useful in reactions such as S N Ar (nucleophilic aromatic substitution), which is essential for the synthesis of various pharmaceuticals and agrochemicals. The triflate leaving group is highly favorable, enabling efficient displacement reactions and facilitating the formation of complex molecular architectures.

In addition to its role as an electrophile, 2,4-dihydroxyphenyldimethylsulfonium triflate has been explored as a catalyst in several chemical transformations. Its unique properties allow it to participate in reactions such as acylation, alkylation, and other carbon-carbon bond-forming reactions. The presence of the sulfonium group enhances the reactivity of the electrophilic center, enabling reactions to proceed under milder conditions and with greater specificity. This versatility has positioned it as a valuable tool for synthetic chemists seeking to optimize reaction conditions and improve product yields.

Moreover, the application of 2,4-dihydroxyphenyldimethylsulfonium triflate extends beyond traditional organic synthesis. Researchers have investigated its use in material science, particularly in the development of polymeric materials. By incorporating this compound into polymer matrices, scientists can enhance the material's properties, such as thermal stability and chemical resistance. This feature is particularly important in industries where durability and performance under various conditions are critical, such as in coatings and electronics.

Despite its potential, the handling and application of 2,4-dihydroxyphenyldimethylsulfonium triflate require careful consideration of safety and environmental factors. Like many sulfonium compounds, it may pose health risks if not managed properly. Therefore, researchers and manufacturers must adhere to safety guidelines and regulatory standards to minimize exposure and environmental impact.

In conclusion, 2,4-dihydroxyphenyldimethylsulfonium triflate is a noteworthy compound that contributes significantly to the fields of organic synthesis and materials science. Its discovery as an effective electrophilic reagent and catalyst has opened new avenues for research and development in synthetic chemistry. As scientists continue to explore its applications, this compound promises to play an essential role in advancing methodologies in organic synthesis and enhancing the properties of advanced materials.