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Trimethylsilyl Blocking Agent
Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.
Trimethyliodosilane; Iodotrimethylsilane, Trimethylsilyl iodide; TMIS
Boiling Point: 106-7°
EINECS Number: 240-171-0
Molecular Weight: 200.10
Alternative Name: TRIMETHYLSILYL IODIDE
Specific Gravity: 1.470
Flashpoint: -2°C (28°F)
HMIS Key: 3-4-1-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Refractive Index: 1.4742
Application: Key reviews.1,2
Reagent for cleavage of ethers, esters, lactones.3
Used to dechlorinate aryl chlorides.4
Allylates aldehydes in the presence of allyl chloride and tin tetraiodide (SNT7946).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. 325-336.
2. Olah, G. et al. In Advances in Silicon Chemistry; Larson, G., Ed.; JAI Press: Greenwich, Co, 1991; Vol. 1, p.1.
3. DePew, K. M. et al. J. Org. Chem. 1999, 121, 11953.
4. Sako, M. et al. J. Org. Chem. 2001, 66, 3610.
5. Masuyama, Y. et al. Tetrahedron Lett. 2005, 46, 2861.
Additional Properties: Dipole moment: 2.46 debye?Hform: -52.2 kcal/moleStabilized with copper granulesVapor pressure, 25°: 40 mm