225649
Trimethylsilyl trifluoromethanesulfonate
99%
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:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
99%
form
liquid
refractive index
n20/D 1.36 (lit.)
bp
77 °C/80 mmHg (lit.)
density
1.228 g/mL at 25 °C (lit.)
functional group
fluoro
triflate
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 has been used in combination with boron trifluoride etherate for the copper-catalyzed asymmetric allylic alkylation (AAA) of allyl bromides, chlorides, and ethers with organolithium reagents in the presence of a chiral ligand.
It can be used:
It may also be used to catalyze:
It can be used:
- As a silylating agent for the synthesis of trimethylsilyl-enol ethers from esters of α-diazoacetoacetic acid.
- To activate benzyl and allyl ethers for the alkylation of sulfides.
- To facilitate the conversion of Diels-Alder adducts of Danishefsky′s diene to cyclohexenones without the formation of methoxy ketone by-product.
- To prepare difluoroboron triflate etherate, a powerful Lewis acid especially in acetonitrile solvent.
- As a reagent in a Dieckmann-like cyclization of ester-imides and diesters.
It may also be used to catalyze:
- Acylation of alcohols with acid anhydrides.
- Reductive coupling of carbonyl compounds with trialkylsilanes to form symmetrical ethers.
- Glycosidation of 4-demethoxydaunomycinones with 1-O-acyl-L-daunosamine derivatives.
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Description
Pricing
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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BF 3? OEt 2 and TMSOTf: A synergistic combination of Lewis acids.
Myers EL, et al.
Chemical Communications (Cambridge, England), 42, 4434-4436 (2006)
A simple method of preparing trimethylsilyl-and tert-butyldimethylsilyl-enol ethers of ?-diazoacetoacetates and their use in the synthesis of a chiral precursor to thienamycin analogs.
Ueda Y, et al.
Canadian Journal of Chemistry, 62(12), 2936-2940 (1984)
Thomas R Hoye et al.
Organic letters, 8(23), 5191-5194 (2006-11-03)
[Structure: see text] Trialkylsilyl triflates effect cyclization of ester-imides such as 2 to produce adducts such as 4a. Trapping of the in situ generated, nucleophilic ketene acetal (cf. 5a) is a key aspect of the transformation. A range of substrates
Novel glycosidation of 4-demethoxyanthracyclinones by the use of trimethylsilyl triflate. Syntheses of optically active 4-demethoxydaunorubicin and 4-demethoxyadriamycin.
Kimura Y, et al.
Bulletin of the Chemical Society of Japan, 59(2), 423-431 (1986)
General ether synthesis under mild acid-free conditions. Trimethylsilyl iodide catalyzed reductive coupling of carbonyl compounds with trialkylsilanes to symmetrical ethers and reductive condensation with alkoxysilanes to unsymmetrical ethers.
Sassaman MB, et al.
The Journal of Organic Chemistry, 52(19), 4314-4319 (1987)
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