TRIMETHYLSILYLACETONITRILE

Product Code: SIT8579.0
CAS No: 18293-53-3
SDS Sheets: EU | US
Pack Size
Quantity
Price
 
5 g
$137.00
25 g
$542.00

Prices listed are EXW price (Morrisville, PA US) in USD. Prices vary depending on currency and Incoterms.

Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    242-169-5
  • Synonyms

    TMSAN
  • HMIS

    3-3-0-X
  • Molecular Formula

    C5H11NSi
  • Molecular Weight (g/mol)

    113.23
  • Purity (%)

    97%
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    49-51/10
  • Density (g/mL)

    0.829
  • Flash Point (˚C)

    50 °C
  • Refractive Index @ 20˚C

    1.4204

Additional Properties

  • Hydrolytic Sensitivity

    4: no reaction with water under neutral conditions
  • 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.

    Safety

  • Packaging Under

    Nitrogen
  • 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
  • Silicon Chemistry, Articles

    Silicon-Based Formation of Carbon-Carbon Bonds – Larson

    Hatanaka and Hiyama first reported the palladium-catalyzed, fluoride-promoted reaction of aryl, alkenyl, allyl, and ethynyltrimethylsilanes with aryl, vinil and allyl halides to form the respective cross-coupled products