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IODOMETHYLTRIMETHYLSILANE
Boiling Point: 140-2°
EINECS Number: 224-123-6
Molecular Weight: 214.12
Specific Gravity: 1.441
Flashpoint: 31°C (88°F)
HMIS Key: 2-3-0-X
Hydrolytic Sensitivity: 3: reacts with aqueous base
Formula: C4H11ISi
Refractive Index: 1.4910
TSCA: TSCA-L
Application: Review of synthetic utility.1
Employed in silyl-methylation of alkynes.2
Converts aldehydes, ketones, ?,?-enones to silyl enol ethers.3
Intermediate for allylic silane synthon, 2-(trimethylsilyl)ethyltriphenylphosphonium iodide.4
Useful for the introduction of the trimethylsilylmethyl group.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. 323-336.
2. Schmid, R. et al. J. Am. Chem. Soc. 1980, 102, 5122.
3. Cazeau, P. et al. Tetrahedron 1987, 43, 2075, 2089.
4. Fleming, I. et al. Synthesis 1979, 446.
5. Vedejs, E. J. Org. Chem. 1985, 50, 2170.
Fieser:
Silanes
Metal-Organics