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Merck
CN

29383

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
EC Number:
248-565-4
UNSPSC Code:
12352103
PubChem Substance ID:
57648366
Beilstein/REAXYS Number:
1868911
MDL number:
MFCD00000406
Assay:
≥98.0% (T)
Form:
liquid

Key Documents

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InChI

1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3

InChI key

FTVLMFQEYACZNP-UHFFFAOYSA-N

SMILES string

C[Si](C)(C)OS(=O)(=O)C(F)(F)F

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.)

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Other Notes

prices for bulk quantities on request

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

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBV8016
BCBS6254V
BCBR5995V
BCBP3932V
BCBM6077V

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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
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
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.
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
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
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