Trimethylsilyl triflate

CAS Number
27607-77-8
EC Number
248-565-4
Abbreviation
TMSOTf

What is Trimethylsilyl triflate?

Trimethylsilyl triflate (CAS 27607-77-8), commonly abbreviated as TMSOTf, is a highly reactive silylating agent used in synthetic chemistry and specialty chemical manufacturing.

Where is Trimethylsilyl triflate used?

  • Pharmaceutical and fine chemical synthesis: installs TMS-protecting groups on alcohols and amines
  • API manufacturing: utilized for carbonyl compounds during multi-step processes
  • Carbohydrate chemistry: activates glycosyl donors in oligosaccharide and glycoconjugate synthesis
  • Polymer and materials chemistry: initiates cationic polymerization and surface silylation
  • Personal care: synthesis of silicone-modified actives and surface-treated powders
  • It transfers trimethylsilyl groups to nucleophilic substrates under mild conditions.

Good to know: Enables selective protection and activation steps that less reactive silylating agents cannot achieve efficiently; particularly useful where conventional silylation routes are too slow or lack the necessary selectivity.

Commercial specifications

  • Purity of at least 98 percent for industrial use
  • Neat standard commercial concentrations
  • Anhydrous solvent solutions available
  • Moisture-sealed packaging to preserve reactivity

Other Names (Synonyms)

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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What are the physical properties of Trimethylsilyl triflate?

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.)

How is Trimethylsilyl triflate classified and handled safely? Learn More

Danger
GHS02· Flammable GHS05· Corrosive

Hazard Statements

H226 Flammable liquid and vapor
H314 Causes severe skin burns and eye damage

Precautionary Statements

P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
P233 Keep container tightly closed.
P240 Ground and bond container and receiving equipment.
P241 Use explosion-proof [electrical/ventilating/lighting/…] equipment.

Which trade and regulatory codes apply to Trimethylsilyl triflate?

HS Code 29310095
UN Number 2920
ADR Class 8
Packing Group II
Storage Class 3 - Flammable liquids
WGK (Germany) 3
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