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29383

Sigma-Aldrich

Trimethylsilyl trifluoromethanesulfonate

produced by Wacker Chemie AG, Burghausen, Germany, ≥98.0% (T)

Synonym(s):

Silane TMS-triflate, TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester

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About This Item

Linear Formula:
CF3SO3Si(CH3)3
CAS Number:
27607-77-8
Molecular Weight:
222.26
Beilstein:
1868911
EC Number:
248-565-4
MDL number:
MFCD00000406
UNSPSC Code:
12352103
PubChem Substance ID:
57648366

grade

produced by Wacker Chemie AG, Burghausen, Germany

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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Other Notes

prices for bulk quantities on request

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H226,H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

Supplementary Hazards

EUH014

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

新产品

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Feng Liu et al.
The Journal of organic chemistry, 74(15), 5699-5702 (2009-06-10)
By treatment with TMSOTf/Et3N, N-(2-cyanoarylmethyl)-substituted acrylamides or beta-ketoamides underwent N-addition cascades under mild conditions to afford the corresponding pyrrolo[1,2-a]pyrimidin-4(6H)-ones as the formal [4 + 2] cycloaddition products in high yields.
Cheng-Chung Wang et al.
Nature protocols, 3(1), 97-113 (2008-01-15)
Detailed protocols for the regioselective protection of individual hydroxyls in monosaccharide units are described here. This expedient methodology incorporates up to seven reaction sequences, obviating the necessity to carry out intermittent tedious work-ups and time-consuming purifications. Using this TMSOTf-catalyzed one-pot
Stevenson Flemer et al.
Journal of peptide science : an official publication of the European Peptide Society, 18(1), 30-36 (2011-10-29)
A methodology is presented for the facile synthesis of Arg-containing peptides modified at the guanidine headgroup as substituted amidine cores. This process allows for the iterative construction of these Arg isosteres while the peptide is being built out on the
Sajal Kumar Maity et al.
Carbohydrate research, 354, 40-48 (2012-05-01)
N-(p-Methylphenylthio)-ε-caprolactam (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides an efficient thiophilic promoter system, capable of activating different thioglycosides. Both 'armed' and 'disarmed' thioglycosyl donors were activated for glycosidic bond formation. Notably, this reagent combination works well in reactivity-based one-pot
Jean-Louis Brochu et al.
Journal of combinatorial chemistry, 10(3), 405-420 (2008-04-19)
A modular, reagent-based approach to obtain different indoline alkaloid-inspired, tetracyclic architectures is developed. With the use of TBSOTf as a Lewis acid, we report here a tandem Michael-based approach that led to the synthesis of a diastereomeric mixture of tetracyclic
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