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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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Izabella Jastrzebska et al.
Steroids, 74(8), 675-683 (2009-05-26)
The reaction of 23-oxotigogenin acetate with TMSOTf in THF afforded the corresponding bisnorcholanic lactone in 60% yield. The analogous reactions carried out in dichloromethane or benzene gave the rearranged products--the isomeric spirostanic ketone (10-15%) and bisfuran (40-42%). Similar products were
Ravindra T Dere et al.
Organic & biomolecular chemistry, 6(12), 2061-2063 (2008-06-06)
A new simple method for the synthesis of alpha-glycosyl thiols is described. Ring-opening of 1,6-anhydrosugars with commercially available bis(trimethylsilyl)sulfide under the action of catalytic amounts of TMSOTf smoothly afforded alpha-glycosyl thiols in very high yields and in a stereospecific way.
Hannah W Mbatia et al.
Photochemistry and photobiology, 88(4), 844-850 (2012-03-13)
ArgenCast-1 (1), a photocage for silver utilizing acyclic polythioether 3,6,12,15-tetrathia-9-azaheptadecane receptor and 4,5-dimethoxy-2-nitrobenzyl (DMNB) chromophore has been prepared using trimethylsilyl trifluoromethanesulfonate-assisted electrophilic aromatic substitution. Metal binding studies with ArgenCast-1 reveal interactions with Ag(+), Hg(2+) and Cu(+), but only Ag(+) coordinates
Pipas Saha et al.
Organic & biomolecular chemistry, 10(43), 8730-8738 (2012-10-06)
Substituted dihydropyrans can be efficiently synthesized in good yields with excellent diastereoselectivity from the reaction of aldehydes or epoxides and ethyl 3-alkyl-3-hydroxy-5-methylhex-5-enoate via an oxonium-ene cyclization reaction catalyzed by trimethylsilyl trifluoromethanesulfonate (TMSOTf) under mild conditions.
Kevin W C Poon et al.
The Journal of organic chemistry, 73(2), 752-755 (2007-12-14)
Employing TMSOTf as an easily available reagent, we have developed a mild and efficient method for the deprotection of both terminal and internal N,0-acetonide functionalities. Various regularly used protecting groups and common organic functional moieties were found to be unaffected
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