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91741

Sigma-Aldrich

Trimethylsilyl trifluoromethanesulfonate

purum, ≥98.0% (T)

Synonym(s):

TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester

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About This Item

Linear Formula:
CF3SO3Si(CH3)3
CAS Number:
27607-77-8
Molecular Weight:
222.26
Beilstein:
1868911
EC Number:
248-565-4
MDL number:
MFCD00000406
UNSPSC Code:
12352101
PubChem Substance ID:
329770075
NACRES:
NA.22

grade

purum

Quality Level

200

Assay

≥98.0% (T)

form

liquid

refractive index

n20/D 1.36 (lit.)

bp

77 °C/80 mmHg (lit.)

density

1.228 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)OS(=O)(=O)C(F)(F)F

InChI

1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3

InChI key

FTVLMFQEYACZNP-UHFFFAOYSA-N

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Application

Trimethylsilyl trifluoromethanesulfonate may be used to catalyze:
  • Allylation of acetals to form homoallyl ethers.
  • Synthesis of 1,2-trans-glycosides.
  • Conversion of alcohols to esters.
  • Aminomethylation of silyl enol ethers with aminomethyl alkyl ethers.
  • Glycosidation of (+)-4-demethoxyanthracyclinones.

Other Notes

Efficient silylating agent and strong Lewis acid catalyst ; Review

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H226,H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

77.0 °F - closed cup

Flash Point(C)

25 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBW0682
BCBL7286V
BCBD8483V
BCBB3628V
BCBB3628

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An extremely fast and efficient acylation reaction of alcohols with acid anhydrides in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst.
Procopiou PA
Chemical Communications (Cambridge, England), (23), 2625-2626 (1996)
T. Bach, H. Brummerhop
J. Prakt. Chem., 341, 410-410 (1999)
Trimethylsilyl trifluoromethanesulfonate (trimethylsilyl triflate) as an excellent glycosidation reagent for anthracycline synthesis. Simple and efficient synthesis of optically pure 4-demethoxydaunorubicin.
Kimura Y
Chemistry Letters (Jpn), 13(4), 501-504 (1984)
Synthesis of homoallyl ethers via allylation of acetals in ionic liquids catalyzed by trimethylsilyl trifluoromethanesulfonate.
Zerth HM
Organic Letters, 5(1), 55-57 (2003)
A novel aminomethylation of silyl enol ethers with aminomethyl ethers catalyzed by iodotrimethylsilane or trimethylsilyl trifluoromethanesulfonate.
Hosomi A
Tetrahedron Letters, 23(5), 547-550 (1982)
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