18293-53-3

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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.

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