Trimethylsilyl 2-(fluorosulfonyl)difluoroacetate
[CAS# 120801-75-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonyl halide
• Name: Trimethylsilyl 2-(fluorosulfonyl)difluoroacetate
• Synonyms: Trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate
• Molecular Formula: C₅H₉F₃O₄SSi
• Molecular Weight: 250.27
• CAS Registry Number: 120801-75-4
• EC Number: 670-657-1
• SMILES: C[Si](C)(C)OC(=O)C(F)(F)S(=O)(=O)F

Properties

• Density: 1.27
• Boiling point: 156 °C
• Refractive index: 1.367
• Flash point: 80 °F

Safety Data

• Hazard Symbols: GHS02;GHS05 Danger
• Risk Statements: H226-H314
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P264-P280-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P321-P363-P370+P378-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Substances or mixtures corrosive to metals	Met. Corr.	1	H290

• Transport Information: UN 2920

Discovery and Applications

Trimethylsilyl 2-(fluorosulfonyl)difluoroacetate is a highly specialized chemical compound with significant applications in organic synthesis, particularly in the development of fluorinated molecules. This compound combines a trimethylsilyl group with a 2-(fluorosulfonyl)difluoroacetate moiety, making it an important reagent for introducing fluorinated functional groups into various substrates.

The discovery of Trimethylsilyl 2-(fluorosulfonyl)difluoroacetate emerged from the need for efficient methods to incorporate fluorine and fluorinated groups into organic molecules. Fluorination is a crucial modification in organic chemistry, as it can enhance the stability, bioactivity, and selectivity of compounds. The development of reagents like Trimethylsilyl 2-(fluorosulfonyl)difluoroacetate addresses the challenge of introducing fluorinated groups in a controlled and effective manner.

This compound is primarily used as a reagent in the synthesis of fluorinated derivatives. The presence of the fluorosulfonyl group provides a strong electrophilic center that can react with nucleophiles, facilitating the introduction of fluorinated moieties into a variety of organic substrates. The trimethylsilyl group, on the other hand, serves as a protecting group, making the compound stable and easy to handle in synthetic procedures.

One of the key applications of Trimethylsilyl 2-(fluorosulfonyl)difluoroacetate is in the synthesis of fluorinated pharmaceuticals and agrochemicals. Fluorinated compounds often exhibit improved pharmacokinetic properties, such as enhanced metabolic stability and increased membrane permeability. Therefore, this reagent is valuable in the pharmaceutical industry for designing and synthesizing new drug candidates with optimized properties.

Another important application of Trimethylsilyl 2-(fluorosulfonyl)difluoroacetate is in the development of fluorinated materials and polymers. The incorporation of fluorinated groups into materials can improve their chemical resistance, thermal stability, and surface properties. This makes the compound useful in creating advanced materials for applications in electronics, coatings, and other high-performance industries.

In addition to its applications in pharmaceuticals and materials science, Trimethylsilyl 2-(fluorosulfonyl)difluoroacetate is also utilized in the development of new catalytic systems. The fluorinated groups in the compound can influence the reactivity and selectivity of catalysts, enabling more efficient and selective chemical transformations. This application is particularly relevant in the field of organofluorine chemistry, where precision and control are essential.

Overall, Trimethylsilyl 2-(fluorosulfonyl)difluoroacetate is a valuable reagent in organic synthesis due to its ability to introduce fluorinated groups into various substrates. Its applications span across pharmaceuticals, materials science, and catalysis, making it an important tool for researchers and industrial chemists working with fluorinated compounds.

References

2004. Reactions of TFDA with Ketones. Synthesis of Difluoromethyl 2,2-Difluorocyclopropyl Ethers. The Journal of Organic Chemistry.
DOI: 10.1021/jo049570y

2014. Recent Advances in the Synthetic Application of Difluorocarbene. Synthesis.
DOI: 10.1055/s-0033-1340856

2024. SuFEx Click Chemistry: Discovery to Applications. Materials Horizons: From Nature to Nanomaterials.
DOI: 10.1007/978-981-97-4596-8_8