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Alkynylsilane Cross-Coupling Agent
The cross-coupling reaction is a highly useful methodology for the formation of carbon-carbon bonds. It involves two reagents, with one typically being a suitable organometallic reagent - the nucleophile - and the other a suitable organic substrate, normally an unsaturated halide, tosylate or similar - the electrophile.
1-Trimethylsilylpropyne; Propynyltrimethylsilane; 1-(Trimethylsilyl)prop-1-yne
Boiling Point: 99-100°
EINECS Number: 228-314-5
Melting Point: -69°
Molecular Weight: 112.25
Specific Gravity: 0.758
Flashpoint: -3°C (27°F)
HMIS Key: 2-4-0-X
Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions
Refractive Index: 1.4091
Application: Forms polymers with very high oxygen permeability.1
Polymerization catalyzed with TaCl5/(C6H5)3Bi.2
Converts aldehydes to 1,3-dienes in presence of Cp2Zr(H)Cl.3
Used in the preparation of alkynylxenon fluoride.5
Useful in silicon-mediated Sonogashira cross-coupling reactions.6
Reference: 1. Masuda, T. et al. J. Am. Chem. Soc. 1983, 105, 7473.
2. Masuda, T. et al. J. Polym. Sci., Part A: Polym. Chem. 1987, 25, 1353.
3. Maeta, H. et al. Tetrahedron Lett. 1992, 33, 5969.
4. F&F: Vol. 2, p 239; Vol. 6, p 638.
5. Schmidt, H. et al. Inorg. Chem. 2004, 43, 1837.
6. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011.