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Product Code: SIE4904.0

Cas No: 1066-54-2

R&D quantities:


Boiling Point: 52°

EINECS Number: 213-919-9

Molecular Weight: 98.22


Specific Gravity: 0.709

Flashpoint: -26°C (-15°F)

HMIS Key: 2-4-1-X

Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions

Formula: C5H10Si

Purity: 98%

Refractive Index: 1.3880


Application: Review of synthetic utility.1
Reacts w/ aryl aldehydes to form diethynylmethane derivatives.10
Useful in the preparation of unsymmetrical diarylacetylenes.11
Ethynylates aromatic compounds.2
Precursor to trimethylsilylethynyl copper reagent.3
Lithiated derivative (n-BuLi treatment) reacts with halotriazines to produce monomers.4
Employed in ortho ethenylation of phenols.5
Undergoes Diels-Alder reactions with butadienes.6
Converts imines to propargyl amines.7
Forms propargylic amines from aldehydes and amines in aqueous system.8
Regioselectively forms either regioisomeric enyne upon addition to propargyl amines depending on catalyst employed.9

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. 569-580.
10. Girard, D. et al. Tetrahedron Lett. 2007, 48, 6022.
11. Mio, M. et al. Org. Lett. 2002, 4, 3199.
2. Austin, W. et al. J. Org. Chem. 1981, 46, 2280.
3. Sakata, H. et al. Tetrahedron Lett. 1987, 28, 5719.
4. Kouveetakis, J. et al. Chem. Mater. 1994, 6, 636.
5. Kobayashi, K.; Yamaguchi, M. Org. Lett. 2001, 3, 241.
6. Paik, S.-J. et al. Org. Lett. 1999, 1, 2045.
7. Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319.
8. Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584.
9. Matsuyama, N. et al. J. Org. Chem. 2009, 74, 3576.


Additional Properties: 310
Doped polymer films are conductive
Vapor pressure, 20°: 214 mm