LITHIUM HEXAMETHYLDISILAZIDE, 95%

Product Code: SIL6467.0
CAS No: 4039-32-1
SDS Sheets: EU | US
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25 g
$51.00
100 g
$164.00
2 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    223-725-6
  • Synonyms

    LITHIUM BIS(TRIMETHYLSILYL)AMIDE
  • HMIS

    3-3-1-X
  • Molecular Formula

    C6H18LiNSi2
  • Molecular Weight (g/mol)

    167.33
  • Purity (%)

    95%
  • TSCA

    Yes
  • Boiling Point (˚C/mmHg)

    114-116/1
  • Melting Point (˚C)

    71-2°

Additional Properties

  • Hydrolytic Sensitivity

    8: reacts rapidly with moisture, water, protic solvents
  • Application

    Review of synthetic utility.1
    Converts aryl halides to anilines.2
    Reacts with ketones and esters in the presence of triethylamine to form the (E)-enol silyl ether with high selectivity.3

    Fieser

    F&F: Vol. 4, p 296; Vol. 5, p 393; Vol. 7, p 197; Vol. 12, p 280; Vol. 13, p 165, p 188, p 257; Vol. 14, p 194; Vol. 15, p 207; Vol. 16, p 16, p 357; Vol. 17, p 33; Vol. 21, p 251.

    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. 356-367.
    2. Lee, S. et al. Org. Lett. 2001, 3, 2729.
    3. Godenschwager, P. F.; Collum, D. B. J. Am. Chem. Soc. 2008, 130, 8726.

    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.

    ALD Material

    Atomic layer deposition (ALD) is a chemically self-limiting deposition technique that is based on the sequential use of a gaseous chemical process. A thin film (as fine as -0.1 Å per cycle) results from repeating the deposition sequence as many times as needed to reach a certain thickness. The major characteristic of the films is the resulting conformality and the controlled deposition manner. Precursor selection is key in ALD processes, namely finding molecules which will have enough reactivity to produce the desired films yet are stable enough to be handled and safely delivered to the reaction chamber.

    Lithium hexamethyldisilazide; Lithium bis(trimethylsilyl)amide; 1,1,1,3,3,3-Hexamethyldisilazane lithium salt

  • Sterically-hindered strong base
  • Degrades slowly at room temperature - solutions exhibit enhanced stability
  • Converts aryl halides to anilines
  • Reacts with ketones and esters in the presence of triethylamine to form the (E)-enol silyl ether with high selectivity
  • Reacts with aryl chlorides or bromides to give anilines
  • 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