225649
Trimethylsilyl trifluoromethanesulfonate
99%
Synonym(s):
TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester
About This Item
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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.)
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
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.
accessory
signalword
Danger
hcodes
Hazard Classifications
Flam. Liq. 3 - Skin Corr. 1B
supp_hazards
Storage Class
3 - Flammable liquids
wgk_germany
WGK 3
flash_point_f
77.0 °F - closed cup
flash_point_c
25 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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