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Product Code: SIM6496.0

Cas No: 31469-15-5

R&D quantities:

100 g
25 g

Interested in a Commercial Order?

Boiling Point: 57° / 15

Molecular Weight: 174.31


Specific Gravity: 0.858

Flashpoint: 43°C (109°F)

HMIS Key: 2-2-1-X

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

Formula: C8H18O2Si

Refractive Index: 1.4150


Application: Review of synthetic utility.1
Initiator for group transfer polymerization.2
With SmI2 converts ketones and aldehydes to silyl enol ethers.3
Cross-couples with aryl bromides.4
Undergoes ?-arylation to form 2-aryl acetates.5
Reacts with fullerenes to form ?-fullerenyl esters.6
Adds to ethyl propiolate in a 2+2 cycloaddition fashion.7

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. 376-380.
2. Webster, O. et al. Science 1983, 222, 39.
3. Hydrio, J. et al. Synthesis 1997, 68, 1.
4. Hama, T. et al. J. Am. Chem. Soc. 2003, 125, 11176.
5. Liu, X.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 5182.
6. Nakamura, E. et al. Org. Lett. 2008, 10, 4923.
7. Quendo, A.; Rousseau, Tetrahedron Lett. 1988, 29, 6443.