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225649

Sigma-Aldrich

Trimethylsilyl trifluoromethanesulfonate

99%

Synonym(s):
TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester
Linear Formula:
CF3SO3Si(CH3)3
CAS Number:
Molecular Weight:
222.26
Beilstein:
1868911
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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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1 of 4

This Item
22614991741279471
form

liquid

form

-

form

liquid

form

liquid

refractive index

n20/D 1.36 (lit.)

refractive index

n20/D 1.385 (lit.)

refractive index

n20/D 1.36 (lit.)

refractive index

n20/D 1.389 (lit.)

bp

77 °C/80 mmHg (lit.)

bp

65-67 °C/12 mmHg (lit.)

bp

77 °C/80 mmHg (lit.)

bp

85-86 °C/12 mmHg (lit.)

density

1.228 g/mL at 25 °C (lit.)

density

1.151 g/mL at 25 °C (lit.)

density

1.228 g/mL at 25 °C (lit.)

density

1.169 g/mL at 25 °C (lit.)

Quality Level

200

Quality Level

-

Quality Level

200

Quality Level

-

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:
  • 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

Product No.
Description
Pricing

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard 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

Certificates of Analysis (COA)

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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)
BF 3? OEt 2 and TMSOTf: A synergistic combination of Lewis acids.
Myers EL, et al.
Chemical Communications (Cambridge, England), 42, 4434-4436 (2006)
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)
Efficient, trimethylsilyl triflate-mediated conversion of Diels-Alder adducts of 1-methoxy-3-[(trimethylsilyl) oxy]-1, 3-butadiene (Danishefsky's diene) to cyclohexenones.
Vorndam PE
The Journal of Organic Chemistry, 55(11), 3693-3695 (1990)

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