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7677-24-9

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TRIMETHYLSILYLCYANIDE

Product Code: SIT8585.0

Cas No: 7677-24-9

R&D quantities:

1.5 kg
$1,020.00
25 g
$83.00
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
  • Releases toxic HCN upon reaction
  • Extremely reactive silylating agent for acids and alcohols
  • Amines and thiols react more slowly than acids and alcohols
  • Does not react with amides, ureas or carbonates
  • Silylates amino acids
  • Nafion SAC-13 has been shown to be a recyclable catalyst for the trimethylsilylation of primary, secondary, and tertiary alcohols in excellent yields and short reaction times
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure
  • 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