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Merck
CN

29383

Sigma-Aldrich

Trimethylsilyl trifluoromethanesulfonate

Wacker Chemie AG, ≥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

Key Documents

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Assay

≥98.0% (T)

form

liquid

manufacturer/tradename

Wacker Chemie AG

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

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBV8016
BCBS6254V
BCBR5995V
BCBP3932V
BCBM6077V

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Christopher G Nasveschuk et al.
The Journal of organic chemistry, 73(2), 612-617 (2007-12-20)
A modular and diastereoselective approach to 2,3,4-trisubstituted and tetrasubstituted tetrahydrofurans is reported. The use of dioxepins containing an embedded vinyl acetal functionality leads to a Lewis acid-mediated [1,3] ring contraction to afford tetrahydrofurans in good yield and excellent diastereoselectivity. The
Hiromichi Fujioka et al.
Chemical communications (Cambridge, England), (29)(29), 4429-4431 (2009-07-15)
The remarkable effect of 2,2'-bipyridyl led to the successful development of the mild and highly chemoselective deprotection method of methoxymethyl (MOM) ethers using the combination of TMSOTf (or TESOTf) and 2,2'-bipyridyl; this method can be applied to the direct conversion
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
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