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PHENYLTHIOTRIMETHYLSILANE
Boiling Point: 72° / 8
EINECS Number: 224-916-7
Molecular Weight: 182.36
Specific Gravity: 0.963
Flashpoint: 33°C (91°F)
HMIS Key: 3-3-1-X
Hydrolytic Sensitivity: 7: reacts slowly with moisture/water
Formula: C9H14SSi
Refractive Index: 1.5320
TSCA: TSCA
Application: Review of synthetic utility.1
Converts adehydes to phenylsulfides.2
Converts aromatic aldehydes to coupled diols with Yb metal.3
Reacts w/ aryl fluorides to provide phenylaryl thioethers.4
Converts enol silyl ethers into vinylsulfides.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. 414-418.
2. Glass, R. Synth. Commun. 1976, 6, 47.
3. Fujiwara, Y. et al. Tetrahedron Lett. 1996, 37. 3465.
4. Liu, C. et al. Synlett 2011, 22, 1143.
5. Degl’innocenti, A. et al. Synlett.1992, 499.
Fieser: F&F: Vol. 10, p 426; Vol. 12, p 535; Vol. 16, p 278.
Silanes
Silanes