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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: 220-844-5
Specific Gravity: 0.945
Flashpoint: 56°C (133°F)
HMIS Key: 2-3-0-X
Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions
Refractive Index: 1.436
Application: Review of synthetic utility.1
Serves as an alcohol equivalent in reaction with aryl iodides.2
Can provide protection for the anomeric center of carbohydrates.3
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. 622-627.
2. >Dibakar, M. et al. Tetrahedron Lett. 2011, 41, 5338.
3. Sowell, C. G. et al. Tetrahedron Lett. 1996, 37, 609.
Fieser: F&F: Vol. 8, p 510.
Additional Properties: Eliminates ethylene in presence of acid or base