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Phenyl-Containing 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.
Triphenylchlorosilane; Chlorotriphenylsilane; Triphenylsilyl chloride
Boiling Point: 188-9° / 3
EINECS Number: 200-989-0
Melting Point: 91-2°
Molecular Weight: 294.85
Specific Gravity: 1.16
Flashpoint: >200°C (>392°F)
HMIS Key: 3-1-1-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Application: Review of synthetic utility.1
Ether derivatives hydrolyze in acid at 0.25% the rate of corresponding Me3Si ethers.2
Reacts with AlBr3 and CO2 to directly form carboxylic acids from arenes and aryl halides.3
Used in the kinetic resolution of secondary alcohols.4
Used In an anion-relay approach to prepare sterically encumbered chiral binaphthols.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. 182-184.
2. Sommer, L. H. Stereochemistry, Mechanism and Silicon; McGraw-Hill: 1965; p. 126.
3. >Nemoto, K. et al. J. Org. Chem. 2010, 75, 7855.
4. >Sheppard, C. I. et al. Org. Lett. 2011, 13, 3794.
5. Maruoka, K. et al. Bull. Chem. Soc. Jpn. 1988, 61, 2975.
Additional Properties: Dipole moment: 2.14 debyeContains triphenylsilanol