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
Recommended Products
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
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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Synthesis of homoallyl ethers via allylation of acetals in ionic liquids catalyzed by trimethylsilyl trifluoromethanesulfonate.
Zerth HM
Organic Letters, 5(1), 55-57 (2003)
Trimethylsilyl trifluoromethanesulfonate as an effective catalyst for glycoside synthesis.
Ogawa T
Carbohydrate Research, 93(1), C6-C9 (1981)
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)
J. Heberle et al.
Silylating Agents, 2nd ed. (1995)
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)
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