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91741

Sigma-Aldrich

Trimethylsilyl trifluoromethanesulfonate

Trimethylsilyl trifluoromethanesulfonate

purum, ≥98.0% (T)

Sinonimo/i:

TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester

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10 ML
CHF 52.80
50 ML
CHF 166.00
250 ML
CHF 731.00

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10 ML
CHF 52.80
50 ML
CHF 166.00
250 ML
CHF 731.00

About This Item

Formula condensata:
CF3SO3Si(CH3)3
Numero CAS:
27607-77-8
Peso molecolare:
222.26
Beilstein:
1868911
Numero CE:
248-565-4
Numero MDL:
MFCD00000406
Codice UNSPSC:
12352101
ID PubChem:
329770075
NACRES:
NA.22

CHF 52.80

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Grado

purum

Livello qualitativo

200

Saggio

≥98.0% (T)

Stato

liquid

Indice di rifrazione

n20/D 1.36 (lit.)

P. ebollizione

77 °C/80 mmHg (lit.)

Densità

1.228 g/mL at 25 °C (lit.)

Gruppo funzionale

fluoro
triflate

Stringa SMILE

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
FTVLMFQEYACZNP-UHFFFAOYSA-N

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Applicazioni

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]

Altre note

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

Pittogrammi

FlameCorrosion
GHS02,GHS05

Avvertenze

Danger

Indicazioni di pericolo

H226,H314

Classi di pericolo

Flam. Liq. 3 - Skin Corr. 1B

Rischi supp

EUH014

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

77.0 °F - closed cup

Punto d’infiammabilità (°C)

25 °C - closed cup

Dispositivi di protezione individuale

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificati d'analisi (COA)

Lot/Batch Number
BCCM5632
BCBW0682
BCBL7286V

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T. Bach, H. Brummerhop
J. Prakt. Chem., 341, 410-410 (1999)
An extremely fast and efficient acylation reaction of alcohols with acid anhydrides in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst.
Procopiou PA
Chemical Communications (Cambridge, England), (23), 2625-2626 (1996)
Trimethylsilyl trifluoromethanesulfonate (trimethylsilyl triflate) as an excellent glycosidation reagent for anthracycline synthesis. Simple and efficient synthesis of optically pure 4-demethoxydaunorubicin.
Kimura Y
Chemistry Letters (Jpn), 13(4), 501-504 (1984)
Synthesis of homoallyl ethers via allylation of acetals in ionic liquids catalyzed by trimethylsilyl trifluoromethanesulfonate.
Zerth HM
Organic Letters, 5(1), 55-57 (2003)
Trimethylsilyl trifluoromethanesulfonate as an effective catalyst for glycoside synthesis.
Ogawa T
Carbohydrate Research, 93(1), C6-C9 (1981)
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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

      Helpful?

  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

      Helpful?

  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.

      Helpful?

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