Trimethylsilyl trifluoromethanesulfonate
Trimethylsilyl trifluoromethanesulfonate (CAS 27607-77-8), with the formula CF3SO3Si(CH3)3 and a molecular weight of 222.26 g/mol, is a potent silylating agent. It is extensively employed in organic synthesis as a Lewis acid catalyst and as a powerful triflating reagent for introducing the triflate group. Its high reactivity makes it invaluable for silylation of alcohols, phenols, and carboxylic acids, and for facilitating various carbon-carbon bond-forming reactions.
- IUPAC
- Silane TMS-triflate,TMS triflate,TMSOTf,Trifluoromethanesulfonic acid trimethylsilylester
Silylation Reagent
Trimethylsilyl trifluoromethanesulfonate serves as an efficient silylating agent, converting alcohols and phenols into their corresponding trimethylsilyl ethers. This transformation is crucial for protecting hydroxyl groups during complex synthetic sequences.
Triflation Reagent
This compound is a source of the highly electrophilic triflate group (CF3SO3-), which can be transferred to various nucleophiles. It is used to activate alcohols for nucleophilic substitution or elimination reactions.
Lewis Acid Catalyst
Acting as a strong Lewis acid, trimethylsilyl trifluoromethanesulfonate can catalyse a range of organic transformations, including Diels-Alder reactions, Friedel-Crafts acylations, and Mukaiyama aldol reactions, often under mild conditions.
Protecting Group Chemistry
The trimethylsilyl (TMS) group introduced by this reagent can function as a temporary protecting group for hydroxyl functions. Its relative ease of introduction and removal makes it a convenient choice in multi-step syntheses.
| Molecular weight | 222.26 |
|---|---|
| Linear formula | CF3SO3Si(CH3)3 |
| Assay | ≥98.0% (T) |
| Boiling point | 77 °C/80 mmHg(lit.) |
| Density | 1.228 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.36(lit.) |
Hazard statements
- H226Flammable liquid and vapour
- H314Causes severe skin burns and eye damage
Precautionary statements
- P280Wear protective gloves, clothing and eye/face protection
- P305IF IN EYES
- P310Immediately call a POISON CENTER or doctor
| Protective equipment | Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 25 °C / 77 °F |
| Transport (UN / ADR) | UN 2920 3(8) / PGII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | C |
| Risk statements (R) | 10-14-34 |
| Safety statements (S) | 16-26-36/37/39-45 |
| Supplemental hazards | Reacts violently with water. |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Trimethylsilyl trifluoromethanesulfonate used for?
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Trimethylsilyl trifluoromethanesulfonate is primarily used as a silylating agent, a triflating reagent, and a Lewis acid catalyst in organic synthesis, particularly for protecting hydroxyl groups and facilitating carbon-carbon bond formation.
What is the CAS number and formula for Trimethylsilyl trifluoromethanesulfonate?
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The CAS number is 27607-77-8, and its molecular formula is CF3SO3Si(CH3)3.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Trimethylsilyl trifluoromethanesulfonate with an assay of ≥98.0% (T). We do not represent this product as USP, BP, or EP grade.
How should Trimethylsilyl trifluoromethanesulfonate be handled safely?
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Trimethylsilyl trifluoromethanesulfonate is a flammable liquid and vapour (H226) that causes severe skin burns and eye damage (H314). It reacts violently with water. Appropriate personal protective equipment, including faceshields, gloves, goggles, and suitable respiratory protection, must be used. Handle in a well-ventilated area and avoid contact with water.
Is Trimethylsilyl trifluoromethanesulfonate a controlled substance?
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The provided data does not indicate that Trimethylsilyl trifluoromethanesulfonate is a controlled substance.
How is Trimethylsilyl trifluoromethanesulfonate shipped and exported?
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As a UN 2920, Class 3 (8), Packing Group II hazardous material, Trimethylsilyl trifluoromethanesulfonate is subject to strict shipping regulations for flammable liquids with corrosive properties. Tech Serve Solutions adheres to all international export and transportation guidelines.
How can I request a sample or quote for Trimethylsilyl trifluoromethanesulfonate?
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To request a sample or quote for Trimethylsilyl trifluoromethanesulfonate, please contact our sales department through the website or by phone, providing your specific requirements.
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