COMMERCIAL
7677-24-9

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TRIMETHYLSILYLCYANIDE

Product Code: SIT8585.0

Cas No: 7677-24-9

R&D quantities:

1.5kg
$1,020.00
25gm
$83.00

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

Formula: C4H9NSi

Refractive Index: 1.3920

TSCA: TSCA

Application: Reviews.1,2
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.

Fieser:

Additional Properties: Contains trimethylchlorosilane
Vapor pressure, 37°: 37.3mm