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.
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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/418/501/product-dating-information-06-25-mk.pdf
225649
Trimethylsilyl trifluoromethanesulfonate
99%
Synonym(s):
TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester
Select a Size
| Size/SKU | Availability | Price |
|---|---|---|
10 g | Available to ship TODAYfromMILWAUKEE | $50.10 |
50 g | Available to ship TODAYfromMILWAUKEE | $188.00 |
250 g | Available to ship TODAYfromMILWAUKEE | $463.00 |
About This Item
Quality Segment
assay
99%
form
liquid
refractive index
n
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
Application
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.[1]
- As a reagent in a Dieckmann-like cyclization of ester-imides and diesters.[2]
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.
1 of 1
This Item | |||
|---|---|---|---|
| assay 99% | assay ≥98.0% (T) | assay 98% | assay 99% |
| Quality Level 200 | Quality Level 200 | Quality Level 200 | Quality Level 100 |
| density 1.228 g/mL at 25 °C (lit.) | density 1.228 g/mL at 25 °C (lit.) | density 1.151 g/mL at 25 °C (lit.) | density 1.169 g/mL at 25 °C (lit.) |
| refractive index n | refractive index n | refractive index n | refractive index n |
| bp 77 °C/80 mmHg (lit.) | bp 77 °C/80 mmHg (lit.) | bp 65-67 °C/12 mmHg (lit.) | bp 85-86 °C/12 mmHg (lit.) |
| form liquid | form liquid | form - | form liquid |
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signalword
Danger
hcodes
Hazard Classifications
Flam. Liq. 3 - Skin Corr. 1B
supp_hazards
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
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How is shipping temperature determined? And how is it related to the product storage temperature?
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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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