18293-53-3

All structures are computer generated. Please rely on the product data below for placing your order. If you see any errors in structures, please email customer service so that they can be addressed.

TRIMETHYLSILYLACETONITRILE

Product Code: SIT8579.0

Cas No: 18293-53-3

R&D quantities:

25 g
$451.00
5 g
$114.00
Silane Cross-Coupling Agent

The cross-coupling reaction is a highly useful methodology for the formation of carbon-carbon bonds. It involves two reagents, with one typically being a suitable organometallic reagent - the nucleophile - and the other a suitable organic substrate, normally an unsaturated halide, tosylate or similar - the electrophile.

Trimethylsilylacetonitrile; TMSAN; Cyanomethyltrimethylsilane
  • Following lithiation with LDA may be alkylated with organobromides
  • Cyanomethylates quinolinium methiodides
  • α-lithio derivative reacts with aldehydes to give (Z)-α,β-unsaturated nitriles
  • Used to cyanomethylation of aryl bromides
  • Under lithium acetate catalysis reacts to cyanomethylate aldehydes and ketones
  • Cyanomethylates aryl bromides
  • Extensive review of silicon based cross-coupling agents: Denmark, S. E. et al. "Organic Reactions, Volume 75" Denmark, S. E. ed., John Wiley and Sons, 233, 2011

    • Boiling Point: 49-51° / 10

    EINECS Number: 242-169-5

    Molecular Weight: 113.23

    Alternative Name: TMSAN

    Specific Gravity: 0.829

    Flashpoint: 50°C (122°F)

    HMIS Key: 3-3-0-X

    Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions

    Formula: C5H11NSi

    Refractive Index: 1.4204

    Application: Review of synthetic utility.1
    Following lithiation with LDA may be alkylated with organobromides.2
    Cyanomethylates quinolinium methiodides.3
    ?-lithio derivative reacts with aldehydes to give (Z)-?,?-unsaturated nitriles.4
    Used to cyanomethylation of aryl bromides.5
    Minireview.6
    Under lithium acetate catalysis reacts to cyanomethylate aldehydes and ketones.7

    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. 564-569.
    2. Mauze, B. et al. J. Organomet. Chem. 1980, 411, 69.
    3. Diaba, F. et al. J. Org. Chem. 2000, 65, 907.
    4. Furuta, K. et al. Bull. Chem. Soc. Jpn. 1984, 57, 2768.
    5. Wu, L.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 15824.
    6. Merino-Montiel, P. Synlett 2009, 507.
    7. Kawano, Y. et al. Chem. Lett. 2005, 34, 1508.

    Fieser: