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226149

Sigma-Aldrich

tert-Butyldimethylsilyl trifluoromethanesulfonate

reagent grade, 98%

Synonym(s):

TBDMS triflate, Trifluoromethanesulfonic acid tert-butyldimethylsilylester

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About This Item

Linear Formula:
CF3SO3Si(CH3)2C(CH3)3
CAS Number:
Molecular Weight:
264.34
Beilstein:
2370068
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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grade

reagent grade

Quality Level

Assay

98%

refractive index

n20/D 1.385 (lit.)

bp

65-67 °C/12 mmHg (lit.)

density

1.151 g/mL at 25 °C (lit.)

functional group

fluoro
triflate

storage temp.

2-8°C

SMILES string

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

InChI

1S/C7H15F3O3SSi/c1-6(2,3)15(4,5)13-14(11,12)7(8,9)10/h1-5H3

InChI key

WLLIXJBWWFGEHT-UHFFFAOYSA-N

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Application

This reagent was used to introduce a bulky tert-butyl dimethylsilyl group onto a cis-bis(alkenyl)oxirane facilitating a room temperature Cope rearrangement to a 2-CF3-4,5-dihydrooxepin.[1]
Together with a thiolane promotes a rapid and efficient chalcogenide-Morita-Baylis-Hillman reaction.[2]

Signal Word

Danger

Hazard Statements

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

98.6 °F - closed cup

Flash Point(C)

37 °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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The Journal of Organic Chemistry, 58, 2287-2287 (1993)
Journal of the Chemical Society. Perkin Transactions 1, 625-625 (1993)
Journal of the Chemical Society. Chemical Communications, 1280-1280 (1988)
Chemistry Letters (Jpn), 33, 438-439 (2004)
Tetrahedron Letters, 47, 3553-3553 (2006)

Questions

1–2 of 2 Questions  
  1. 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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  2. 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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