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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.
Trimethysilyl Cyanide; Trimethylsilylnitrile; Cyanotrimethylsilane; TMSCN
Boiling Point: 118-9°
EINECS Number: 231-657-3
Melting Point: 11-12°
Molecular Weight: 99.21
Alternative Name: TRIMETHYLSILYLNITRILE
Specific Gravity: 0.744
Flashpoint: 1°C (34°F)
HMIS Key: 4-4-1-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Refractive Index: 1.3920
Undergoes very rapid Al-MCM-41-catalyzed reactions with aldehydes and ketones.10
Converts alcohols to isocyanides in good yields.11
Oxidatively ?-cyanates tertiary amines.12
Employed in 3-component, one-pot Strecker conversion of aldehydes to ?-amino nitriles.13,14
Efficient conversion of carbonyls to cyanohydrins catalyzed by Cu(II) trifluoromethanesulfonate.3
Treatment with methanol generates HCN solutions.4
Adds to aldehydes with high stereoselectivity.5
Adds HCN to benzylhydrazones.6
Opens epoxides with high enantioselectivity.7
Converts tertiary alcohols to isocyanides.8
Used to protect aldehydes in formation of aldehyde-functional Grignard reagents.9
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. 184-189.
10. Iwanami, K. et al. J. Chem. Soc., Chem. Commun. 2008, 1002.
11. >Okada, I.; Kitano, Y. Synthesis, 2011, 3997.
12. Han. W.; Ofial, A. R. J. Chem. Soc., Chem. Commun. 2009, 5024.
13. Karmekar, B.; Banerji, J. Tetrahedron Lett. 2010, 51, 2748.
14. Niknam, K. et al. Tetrahedron Lett. 2010, 51, 2959.
2. Rasmussen, J. et al. In Advances in Silicon Chemistry; Larson, G., Ed.; JAI Press: Greenwich, Co, 1991; Vol. 1, p65.
3. Saravanan, D. et al. Tetrahedron Lett. 1998, 39, 3823.
4. Vachel, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
5. Belokon, Y. N.; North, M. Org. Lett. 2000, 2, 1617.
6. Manabe, K. et al. J. Org. Chem. 1999, 64, 8054.
7. Schaus, S. E.; Jacobsen, E. N. Org. Lett. 2000, 2, 1001.
8. Kitano, Y. et al. Synthesis 2001, 437.
9. Liu, C.-Y. et al. Org. Lett. 2006, 8, 617.
Additional Properties: Contains trimethylchlorosilaneVapor pressure, 37°: 37.3mm