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Merck
CN

225649

Trimethylsilyl trifluoromethanesulfonate

99%

Synonym(s):

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
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24853510
EC Number:
248-565-4
Beilstein/REAXYS Number:
1868911
MDL number:
MFCD00000406
Assay:
99%
Form:
liquid

Key Documents

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InChI key

FTVLMFQEYACZNP-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

99%

form

liquid

refractive index

n20/D 1.36 (lit.)

bp

77 °C/80 mmHg (lit.)

density

1.228 g/mL at 25 °C (lit.)

functional group

fluoro, triflate

Quality Level

200

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Application

Trimethylsilyl trifluoromethanesulfonate has been used in combination with boron trifluoride etherate for the copper-catalyzed asymmetric allylic alkylation (AAA) of allyl bromides, chlorides, and ethers with organolithium reagents in the presence of a chiral ligand.
It can be used:
  • As a silylating agent for the synthesis of trimethylsilyl-enol ethers from esters of α-diazoacetoacetic acid.
  • To activate benzyl and allyl ethers for the alkylation of sulfides.
  • To facilitate the conversion of Diels-Alder adducts of Danishefsky′s diene to cyclohexenones without the formation of methoxy ketone by-product.
  • To prepare difluoroboron triflate etherate, a powerful Lewis acid especially in acetonitrile solvent.
  • As a reagent in a Dieckmann-like cyclization of ester-imides and diesters.

It may also be used to catalyze:
  • Acylation of alcohols with acid anhydrides.
  • Reductive coupling of carbonyl compounds with trialkylsilanes to form symmetrical ethers.
  • Glycosidation of 4-demethoxydaunomycinones with 1-O-acyl-L-daunosamine derivatives.

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

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCX9495
MKCV5462
MKCT7793
MKCR9262
MKCM5773

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Novel glycosidation of 4-demethoxyanthracyclinones by the use of trimethylsilyl triflate. Syntheses of optically active 4-demethoxydaunorubicin and 4-demethoxyadriamycin.
Kimura Y, et al.
Bulletin of the Chemical Society of Japan, 59(2), 423-431 (1986)
Journal of the Chemical Society. Chemical Communications, 755-755 (1993)
Efficient, trimethylsilyl triflate-mediated conversion of Diels-Alder adducts of 1-methoxy-3-[(trimethylsilyl) oxy]-1, 3-butadiene (Danishefsky's diene) to cyclohexenones.
Vorndam PE
The Journal of Organic Chemistry, 55(11), 3693-3695 (1990)
Eddie L Myers et al.
Chemical communications (Cambridge, England), (42), 4434-4436 (2006-10-24)
The combination of BF3.OEt2 and TMSOTf gives BF2OTf.OEt2, which is a more powerful Lewis acid than its components and especially effective in CH3CN solvent; the complex formed has been characterised by 1H, 19F, 11B and 31P (using Et3PO as an
Method for sulfide S-benzylation or S-allylation using trimethylsilyl triflate activated benzyl or allyl ethers.
Vedejs E & Eustache J.
The Journal of Organic Chemistry, 46(16), 3353-3354 (1981)
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