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DIPHENYLSILANE
Boiling Point: 95-7° / 13
EINECS Number: 212-271-4
Molecular Weight: 184.31
Specific Gravity: 0.9969
Flashpoint: 98°C (208°F)
HMIS Key: 2-1-1-X
Hydrolytic Sensitivity: 3: reacts with aqueous base
Formula: C12H12Si
Refractive Index: 1.5795
TSCA: TSCA
Application: Converts amides to aldehydes in combination with Ti(OiPr)4.2
Selective reduction of esters.3
Silylates 1,2-diols in presence of tris(pentafluorophenyl)borane.4
Used in enantioselective reduction of imines.5
Reducing agent.1
Reference: 2. Bower, S. et al. Angew. Chem., Int. Ed. Engl. 1996, 35, 1515.
3. Onta, T. et al. Tetrahedron Lett. 1999, 40, 6963.
4. Blackwell, J. M. et al. J. Org. Chem. 1999, 64, 4887.
5. Takai, I. et al. Organometallics 1999, 18, 2271.
Fieser: F&F: Vol. 1, p 348.
Silanes
Silicon-Based Reducing Agents
Enabling Synthetic Organic Transformations
Key Organosilane Reductions – Larson
The Synthesis of Gliflozins – Larson
Organosilane Reductions with Polymethylhydrosiloxanes – Larson
Tetramethyldisiloxane: A Practical Organosilane Reducing Agent – Larson