Trimethylsilyl triflate
Description
Trimethylsilyl triflate (CAS 27607-77-8), commonly abbreviated as TMSOTf, is a highly reactive silylating agent used across synthetic chemistry and specialty chemical manufacturing. It transfers trimethylsilyl groups to nucleophilic substrates under mild conditions.
This reagent enables selective protection and activation steps that less reactive silylating agents cannot achieve efficiently. In pharmaceutical and fine chemical synthesis, it is used to install TMS-protecting groups on alcohols and amines.
It is also utilized for carbonyl compounds during multi-step API manufacturing. It activates glycosyl donors in carbohydrate chemistry, making it a standard reagent in oligosaccharide and glycoconjugate synthesis processes.
In polymer and materials chemistry, it initiates cationic polymerization and surface silylation processes where controlled reactivity is critical. This ensures product consistency across various industrial applications.
Personal care ingredient manufacturers use it in the synthesis of silicone-modified actives and surface-treated powders. This is particularly useful where conventional silylation routes are too slow or lack the necessary selectivity.
TMSOTf is supplied as a colorless to pale yellow liquid, typically in moisture-sealed packaging to preserve reactivity. Standard commercial concentrations are neat with a purity of at least 98 percent for industrial use.
Anhydrous solvent solutions are also available, suited for direct use in synthesis. Technical and high-purity reagent grades are offered, with the latter meeting specifications required for pharmaceutical intermediate production.
Physical Properties
| Melting Point | <25 °C |
| Boiling Point | 140-141 °C |
| Density | 1.225 g/cm³ |
| Flash Point | 78 °F |
| Appearance | clear colourless to light brown fuming liquid |
| Color | Clear colorless to light brown |
| Form | Fuming Liquid |
| Water Solubility | REACTS |
| Vapor Pressure | 4.7 hPa (20 °C) |
| Refractive Index | n 20/D 1.36(lit.) |
Safety & Handling (Learn More)
Trade & Regulatory
| HS Code | 29310095 |
| UN Number | 2920 |
| ADR Class | 8 |
| Packing Group | II |
| Storage Class | 3 - Flammable liquids |
| WGK (Germany) | 3 |
Documentation
Other Names
trimethylsilyl trifluoromethanesulfonate|TMS triflate|Trimethylsilyl trifluoromethanesulphonate|Trimethylsilyl trifluoromethylsulfonate|Methanesulfonic acid, trifluoro-, trimethylsilyl ester|Z84V0CBH9J|trimethylsilanol trifluoromethanesulfonate|Methanesulfonic acid, 1,1,1-trifluoro-, trimethylsilyl ester|TMSOTf
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