Skip to Content
MilliporeSigma
All Photos(1)

Documents

91741

Sigma-Aldrich

Trimethylsilyl trifluoromethanesulfonate

purum, ≥98.0% (T)

Synonym(s):

TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
CF3SO3Si(CH3)3
CAS Number:
27607-77-8
Molecular Weight:
222.26
Beilstein/REAXYS Number:
1868911
EC Number:
248-565-4
MDL number:
MFCD00000406
UNSPSC Code:
12352101
PubChem Substance ID:
329770075
NACRES:
NA.22

grade

purum

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

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

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

hcodes

H226,H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

supp_hazards

EUH014

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCBW0682
BCBL7286V
BCBD8483V
BCBB3628V
BCBB3628

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
T. Bach, H. Brummerhop
J. Prakt. Chem., 341, 410-410 (1999)
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)
Trimethylsilyl trifluoromethanesulfonate as an effective catalyst for glycoside synthesis.
Ogawa T
Carbohydrate Research, 93(1), C6-C9 (1981)
Synthesis of homoallyl ethers via allylation of acetals in ionic liquids catalyzed by trimethylsilyl trifluoromethanesulfonate.
Zerth HM
Organic Letters, 5(1), 55-57 (2003)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service