trimethylsilyl trifluoromethanesulfonate

• ChemBase ID: 99824
• Molecular Formular: C4H9F3O3SSi
• Molecular Mass: 222.2581696
• Monoisotopic Mass: 221.99937634
• SMILES: S(=O)(=O)(O[Si](C)(C)C)C(F)(F)F
• Canonical SMILES: FC(S(=O)(=O)O[Si](C)(C)C)(F)F
• InChI: InChI=1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3
• InChIKey: FTVLMFQEYACZNP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trimethylsilyl trifluoromethanesulfonate
• IUPAC Traditional name: trimethylsilyl triflate
• Synonyms: Trimethylsilyl trifluoromethanesulphonate 98%; TMS-OTf; Trifluoromethanesulfonic acid trimethylsilyl ester; Trimethylsilyl trifluoromethanesulfonate; TMSOTf; Silane TMS-triflate; TMS triflate; Trifluoromethanesulfonic acid trimethylsilylester; Trimethylsilyl trifluoromethanesulfonate; 三氟甲烷磺酸三甲基硅烷酯; TMS 三氟甲基磺酸酯; 三甲基硅基三氟甲烷磺酸酯; 硅烷 TMS-三氟甲磺酸酯; 三氟甲磺酸三甲基硅酯

Database IDs

• CAS Number: 27607-77-8
• EC Number: 248-565-4
• MDL Number: MFCD00000406
• Beilstein Number: 1868911
• Merck Index: 149719
• PubChem SID: 24857680; 162086071; 24889548; 24853510
• PubChem CID: 65367

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.0977
• LogD (pH = 7.4): 3.0977
• Log P: 3.0977
• Molar Refractivity: 33.1078 cm^3
• Polarizability: 15.741947 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 37-40°C/12mm; 39-40°C/12mm; 77 °C/80 mmHg(lit.)
• Flash Point: 25 °C; 25°C; 25°C(77°F); 77 °F
• Density: 1.225; 1.228; 1.228 g/mL at 25 °C(lit.)
• Refractive Index: 1.36; 1.3620; n20/D 1.36(lit.)

Safety Information

• Storage Warning: Corrosive/Flammable/Air Sensitive/Moisture Sensitive/Store under Argon/Keep Cold; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 2920; UN2924
• German water hazard class: 3
• Hazard Class: 3; 8
• Packing Group: 2; III
• Risk Statements: 10-14-34
• Safety Statements: 16-26-36/37/39-45; 8-20-26-30-36/37/39-45-60
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H314; H314-H318-H226
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2
• Supplemental Hazard Statements: Reacts violently with water.

Product Information

• Purity: ≥98.0% (T); 97%; 99%
• Grade: produced by Wacker; purum
• Linear Formula: CF3SO3Si(CH3)3

DETAILS

Apollo Scientific Ltd - PC7867

Lewis acid & highly reactive silylating reagent see:Synthesis, 1 (1982); Adv. Silicon Chem., 1, 189 (1991)

Sigma Aldrich - 225649

Application
Used to prepare difluoroboron triflate etherate a powerful Lewis acid especially in acetonitrile solvent.1 Reagent used in a Dieckmann-like cyclization of ester-imides and diesters.2
Packaging
10, 50 g in ampule

Sigma Aldrich - 29383

Other Notes
prices for bulk quantities on request
Packaging
1 kg in glass bottle
250 g in glass bottle

Sigma Aldrich - 91741

Other Notes
Efficient silylating agent and strong Lewis acid catalyst 1,2; Review 3

REFERENCES

• Trialkylsilyl perfluoroalkanesulfonates are highly reactive silylating agents (see Appendix 4) and Lewis acids: Synthesis, 1 (1982); Adv. Silicon Chem., 1, 189 (1991).
• Amides can be N,O-disilylated with TMSOTf: Org. Synth. Coll., 9, 516 (1998). For conversion of carbonyl compounds to silyl enol ethers, see, e.g.: J. Org. Chem., 58, 1449 (1993); Org. Synth. Coll., 9, 548 (1998). The reaction rate in triethylamine is almost 10⁹ times faster than with TMS chloride: Liebigs Ann. Chem., 1718 (1980).
• In general, TMSOTf has a much greater tendency to give C-silylation than TMS chloride. With esters C-silylation usually predominates: Synthesis, 867 (1977); Liebigs Ann. Chem., 816 (1983). Nitriles are C-silylated: Synthesis, 636 (1977); Synth. Commun., 18, 2111 (1988). Electron-rich alkenes, e.g. ketene acetals, as well as electron-rich aromatics such as indoles and pyrroles also undergo C-silylation: Synthesis, 928, 929 (1984):
  
• tert-Butyl esters are cleaved directly to trimethylsilyl esters. Benzyl esters are unaffected, permitting selective cleavage: Synthesis, 545 (1980).
• TMSOTf has numerous applications as a Lewis acid catalyst, notably in mediating, under very mild conditions, crossed aldol condensations between silyl enol ethers and acetals: J. Am. Chem. Soc., 102, 3248 (1980); Tetrahedron, 44, 4259 (1988); Org. Synth. Coll., 9, 642 (1998).
• For a brief feature on uses of the reagent, see: Synlett, 1940 (2003).