COMMERCIAL
27607-77-8

All structures are computer generated. Please rely on the product data below for placing your order. If you see any errors in structures, please email customer service so that they can be addressed.

TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE

Product Code: SIT8620.0

Cas No: 27607-77-8

R&D quantities:

2.5 kg
$1,265.00
100 g
$162.00
25 g
$50.00

Interested in a Commercial Order?

Boiling Point: 140-1°

EINECS Number: 248-565-4

Molecular Weight: 222.25

Alternative Name: TRIMETHYLSILYLTRIFLATE

Specific Gravity: 1.225

Flashpoint: 40°C (104°F)

HMIS Key: 3-2-1-X

Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents

Formula: C4H9F3O3SSi

Refractive Index: 1.360

TSCA: TSCA

Application: Review of synthetic utility.1
Review on organosilane protecting groups.2
Reacts with ketones to form silyl enol ethers; Review.3
Enhances the addition of terminal acetylenes to aldehydes.4
Used in the nickel-catalyzed direct phenylation of C-H bonds in heteroaromatic system such as benzoxazoles.5

Reference: 1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 518-537.
2. Larson, G. L. “Silicon-Based Blocking Agents” Gelest, Inc. 2014.
3. Simchen, G. In Advances in Silicon Chemistry; Larson, G., Ed.; JAI Press: Greenwich, Co, 1991; Vol. 1, p189.
4. Downey, C. W. et al. J. Org. Chem. 2009, 74, 2904.
5. Hachilya, H. et al. Angew. Chem., Int. Ed. Engl. 2010, 49, 2202.

Fieser: F&F: Vol. 6, p 639; Vol. 8, p 497; Vol. 10, p 438; Vol. 11, p 584; Vol. 12, p 543; Vol. 13, p 118, p 149, p 187, p 321, p 329; Vol. 14, p 119, p 202, p 259, p 321, p 333; Vol. 15, p 66, p 102, p 108, p 346; Vol. 16, p 49, p 112, p 138, p 278, p 363; Vol. 17, p 26, p 379; Vol. 18, p 23, p 57, p 383; Vol. 20, p 408; Vol. 21, p 460.

Additional Properties: 405
Vapor pressure, 26°: 14 mm