Trimethylsilyl trifluoromethanesulfonate
[CAS# 27607-77-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Silane
• Name: Trimethylsilyl trifluoromethanesulfonate
• Synonyms: Trifluoromethanesulfonic acid trimethylsilyl ester; Trimethylsilyl triflate
• Molecular Formula: C₄H₉F₃O₃SSi
• Molecular Weight: 222.25
• CAS Registry Number: 27607-77-8
• EC Number: 248-565-4
• SMILES: C[Si](C)(C)OS(=O)(=O)C(F)(F)F

Properties

• Density: 1.225
• Boiling point: 140 °C
• Refractive index: 1.36-1.362
• Flash point: 25 °C
• Water solubility: REACTS

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H226-H314-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P261-P264-P271-P280-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P319-P321-P363-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Skin corrosion	Skin Corr.	1B	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1A	H314
Acute toxicity	Acute Tox.	4	H332
Flammable liquids	Flam. Liq.	2	H225
Acute toxicity	Acute Tox.	3	H331

• Transport Information: UN 2920

Discovery and Applications

Trimethylsilyl trifluoromethanesulfonate is a valuable chemical compound used primarily as a reagent in organic synthesis. This substance combines a trimethylsilyl group with a trifluoromethanesulfonate moiety, making it a potent and versatile tool in various chemical transformations.

The discovery of trimethylsilyl trifluoromethanesulfonate emerged from the ongoing research into silylating agents and their applications in organic chemistry. The trifluoromethanesulfonate group is known for its strong electron-withdrawing properties, while the trimethylsilyl group provides a favorable site for reactions involving silicon chemistry. The combination of these groups enhances the reactivity of the compound, making it an effective reagent in numerous synthetic processes.

One of the primary applications of trimethylsilyl trifluoromethanesulfonate is as a silylating agent. It is commonly used to convert alcohols into their corresponding trimethylsilyl ethers. This transformation is crucial in protecting hydroxyl groups during chemical synthesis, allowing for selective reactions at other functional sites. The silyl ether protection is particularly valuable in complex organic synthesis where multiple functional groups are present, ensuring that certain groups remain unchanged while others undergo modification.

Additionally, trimethylsilyl trifluoromethanesulfonate is employed in the field of fluorination chemistry. Its trifluoromethanesulfonate group can participate in reactions that introduce fluorine-containing groups into organic molecules. Fluorination is a key modification in medicinal chemistry and material science, where fluorine atoms can significantly influence the physical and chemical properties of compounds. The use of trimethylsilyl trifluoromethanesulfonate in these reactions allows for the precise incorporation of fluorine into target molecules, facilitating the development of new pharmaceuticals and advanced materials.

The compound is also used in the synthesis of various functionalized silicon-containing compounds. For instance, it can act as a reagent in the preparation of silicon-based intermediates that are essential in the production of silicones, which are widely used in industrial applications. These include coatings, sealants, and elastomers, where the unique properties of silicon-containing compounds provide superior performance characteristics.

Moreover, trimethylsilyl trifluoromethanesulfonate is valuable in the development of new materials with specific properties. The ability to introduce silyl and trifluoromethanesulfonate groups into polymer systems can alter their solubility, thermal stability, and reactivity. This makes the compound a useful tool in designing advanced materials for a variety of applications, including electronics and coatings.

Overall, trimethylsilyl trifluoromethanesulfonate is an important reagent in organic synthesis, offering significant advantages in silylation, fluorination, and material science. Its unique combination of silyl and trifluoromethanesulfonate groups provides versatility and reactivity, making it a valuable asset in chemical research and industrial applications.

References

2024. Synthetic Study of Bio-functional Glycans. Methods in Molecular Biology, 2763.
DOI: 10.1007/978-1-0716-3670-1_4

2022. Synthetic Strategies for FRET-Enabled Carbohydrate Active Enzyme Probes. Methods in Molecular Biology, 2370.
DOI: 10.1007/978-1-0716-1685-7_12

2021. Friedel-Crafts Addition of Indoles to Nitrones Promoted by Trimethylsilyl Trifluoromethanesulfonate. Organic Letters, 23(15).
DOI: 10.1021/acs.orglett.1c02054