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91741

Sigma-Aldrich

Trimethylsilyl trifluoromethanesulfonate

Trimethylsilyl trifluoromethanesulfonate

purum, ≥98.0% (T)

Synonym(s):

TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester

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About This Item

Linear Formula:
CF3SO3Si(CH3)3
CAS Number:
Molecular Weight:
222.26
Beilstein:
1868911
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
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grade

purum

Quality Level

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.)

functional group

fluoro
triflate

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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Application

Trimethylsilyl trifluoromethanesulfonate may be used to catalyze:
  • Allylation of acetals to form homoallyl ethers.[1]
  • Synthesis of 1,2-trans-glycosides.[2]
  • Conversion of alcohols to esters.[3]
  • Aminomethylation of silyl enol ethers with aminomethyl alkyl ethers.[4]
  • Glycosidation of (+)-4-demethoxyanthracyclinones.[5]

Other Notes

Efficient silylating agent and strong Lewis acid catalyst [6][7]; Review [8]

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

Supplementary Hazards

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

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Certificates of Analysis (COA)

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Trimethylsilyl trifluoromethanesulfonate as an effective catalyst for glycoside synthesis.
Ogawa T
Carbohydrate Research, 93(1), C6-C9 (1981)
Synthesis of homoallyl ethers via allylation of acetals in ionic liquids catalyzed by trimethylsilyl trifluoromethanesulfonate.
Zerth HM
Organic Letters, 5(1), 55-57 (2003)
T. Bach, H. Brummerhop
J. Prakt. Chem., 341, 410-410 (1999)
J. Heberle et al.
Silylating Agents, 2nd ed. (1995)
A novel aminomethylation of silyl enol ethers with aminomethyl ethers catalyzed by iodotrimethylsilane or trimethylsilyl trifluoromethanesulfonate.
Hosomi A
Tetrahedron Letters, 23(5), 547-550 (1982)

Questions

1–3 of 3 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. Does this product come in a glass bottle? I would prefer not to buy an ampule.

    1 answer
    1. This product is packaged in amber glass bottles with ETFE screw caps.

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