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Specialty Silicon-Based 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.
EINECS Number: 240-601-7
Specific Gravity: 1.375
Flashpoint: 41°C (106°F)
HMIS Key: 3-2-1-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Refractive Index: 1.4650
Application: Review of synthetic utility.1
Modifies ITO electrodes allowing bonding of polyvinylpyridine.2
Forms oxasilacycles via a silylation/free-radical addition sequence. The resulting oxasilacycles can be oxidized and desilylated to diols.3
Used in a silicon-based templated cyclization to produce 1,4 diols.4,5
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. 85-92.
2. Privman, M. et al. J. Am. Chem. Soc. 2009, 131, 1314.
3. Newlander, K. A. et al. J. Org. Chem. 1997, 62, 6726.
4. Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500.
5. Lejeune, J.; Lallemand, J. Y. Tetrahedron Lett. 1992, 33, 2977.
Additional Properties: Precursor to various bromomethylsilanes and their Grignard or Li derivatives