Trimethylsilyl trifluoromethanesulfonate CAS 27607-77-8

CAS 27607-77-8
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Product Name: Trimethylsilyl trifluoromethanesulfonate​
CAS Number: 27607-77-8​
Synonyms: TMS triflate; Trimethylsilyl triflate; TMSOTf​
Molecular Formula: C₄H₉F₃O₃SSi​
Molecular Weight: 222.26 g/mol​
1. Physical and Chemical Properties​
​
Property​
Specification​
Appearance​
Colorless to pale yellow transparent liquid​
Boiling Point​
142-145 °C (at 760 mmHg)​
Melting Point​
-77 °C​
Density​
1.220 g/mL (at 25 °C)​
Refractive Index​
n₂₀/D 1.3880-1.3920​
Flash Point​
38 °C (closed cup)​
Solubility​
Soluble in organic solvents such as dichloromethane, chloroform, ether, and toluene; reacts violently with water​
Stability​
Stable under dry and inert conditions; sensitive to moisture, air, and strong bases​
​
2. Quality Specifications​
​
Parameter​
Standard​
Purity (GC)​
≥ 98.0%​
Water Content (Karl Fischer)​
≤ 0.1%​
Free Trifluoromethanesulfonic Acid​
≤ 0.5%​
Metal Impurities​
≤ 10 ppm (each)​
​
3. Applications​
Trimethylsilyl trifluoromethanesulfonate (TMSOTf) is a highly reactive and versatile organosilicon reagent, widely used in organic synthesis for:​
  • Silylation Reactions: Protecting hydroxyl (-OH), amino (-NH₂), and carboxyl (-COOH) groups by forming trimethylsilyl (TMS) ethers/amines/esters.​
  • Friedel-Crafts Reactions: Acting as a strong Lewis acid catalyst for alkylation, acylation, and condensation reactions.​
  • Glycosylation Reactions: Promoting the formation of glycosidic bonds in carbohydrate synthesis.​
  • Desilylation Reactions: Selective cleavage of TMS protecting groups under mild conditions.​
  • Other applications: Catalyzing Diels-Alder reactions, rearrangements, and heterocycle synthesis.