91741
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:
Molecular Weight:
222.26
Beilstein:
1868911
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
grade
purum
Quality Level
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
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Flam. Liq. 3 - Skin Corr. 1B
Supplementary Hazards
WGK
WGK 3
Flash Point(F)
77.0 °F
Flash Point(C)
25 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
危险化学品
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T. Bach, H. Brummerhop
J. Prakt. Chem., 341, 410-410 (1999)
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)
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)
J. Heberle et al.
Silylating Agents, 2nd ed. (1995)
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