Description
Additional Properties
Hydrolytic Sensitivity 8: reacts rapidly with moisture, water, protic solvents 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. Safety
Packaged Over Copper
Packaging Under Nitrogen 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
Extremely reactive silylating agent
Used with HMDS for hindered alcohols
Forms enol silyl ethers with ketones and SIT8620.0
Nafion SAC-13 has been shown to be a recyclable catalyst for the trimethylsilylation of primary, secondary, and tertiary alcohols in excellent yields and short reaction times
Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure
