tert-Butyldimethylsilyl trifluoromethanesulfonate
tert-Butyldimethylsilyl trifluoromethanesulfonate (CAS: 69739-34-0), with the chemical formula CF3SO3Si(CH3)2C(CH3)3, is a valuable reagent in organic synthesis. Its molecular weight is 264.34 g/mol. This compound is primarily utilised for the introduction of the bulky tert-butyldimethylsilyl (TBDMS) protecting group onto alcohols and other nucleophilic functionalities. It serves as a key intermediate in complex multi-step syntheses, particularly in pharmaceutical and fine chemical research and development.
- IUPAC
- TBDMS triflate,Trifluoromethanesulfonic acid tert-butyldimethylsilylester
- Synonyms
- TBDMS triflateTrifluoromethanesulfonic acid tert-butyldimethylsilylester
Introduction of TBDMS Protecting Groups
This reagent is an effective silylating agent for the protection of alcohols, phenols, and amines. The tert-butyldimethylsilyl group is widely employed due to its stability under various reaction conditions and its selective removal.
Facilitating Complex Rearrangements
It has been documented for use in facilitating complex organic transformations, such as enabling a room temperature Cope rearrangement of cis-bis(alkenyl)oxiranes. This application highlights its utility in stereoselective synthesis.
Organic Synthesis Intermediate
As a silicon-based reagent, it plays a role in advanced organic synthesis. Its reactivity allows for the controlled formation of silicon-oxygen or silicon-nitrogen bonds, crucial for building complex molecular architectures.
| Molecular weight | 264.34 |
|---|---|
| Linear formula | CF3SO3Si(CH3)2C(CH3)3 |
| Assay | ≥98.0% (T) |
| Boiling point | 65-67 °C/12 mmHg(lit.) |
| Density | 1.151 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.385(lit.) |
| Storage temperature | 2-8°C |
| Application | This reagent was used to introduce a bulky tert-butyl dimethylsilyl group onto a cis-bis(alkenyl)oxirane facilitating a room temperature Cope rearrangement to a 2-CF3-4,5-dihydrooxepin.1 |
Hazard statements
- H226Flammable liquid and vapour
- H314Causes severe skin burns and eye damage
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- 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 | 37 °C / 98.6 °F |
| Transport (UN / ADR) | UN 2920 3(8) / PGII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | C |
| Risk statements (R) | 10-34-37 |
| Safety statements (S) | 26-36/37/39-45 |
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 tert-Butyldimethylsilyl trifluoromethanesulfonate used for?
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tert-Butyldimethylsilyl trifluoromethanesulfonate is primarily used as a silylating agent to introduce the tert-butyldimethylsilyl (TBDMS) protecting group onto alcohols and other nucleophiles in organic synthesis. It also finds application in facilitating complex rearrangements.
What are the CAS number and chemical formula for this product?
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The CAS number is 69739-34-0, and the chemical formula is CF3SO3Si(CH3)2C(CH3)3.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies tert-Butyldimethylsilyl trifluoromethanesulfonate with an assay of ≥98.0% (T). This product is not classified as USP, BP, or EP grade.
How should tert-Butyldimethylsilyl trifluoromethanesulfonate be handled safely?
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Danger: This compound is flammable (H226), causes severe skin burns and eye damage (H314), and may cause respiratory irritation (H335). Always use appropriate personal protective equipment, including face shields, goggles, gloves, and a suitable respirator. Handle only in a well-ventilated area or fume hood.
Is this chemical packed and shipped internationally by TSS?
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Yes, Tech Serve Solutions specialises in the global supply and export of fine chemicals, including tert-Butyldimethylsilyl trifluoromethanesulfonate.
How can I request a sample or quote for this product?
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To request a sample or a quote, please contact our sales team through the provided channels on the Tech Serve Solutions website.
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