4039-32-1

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LITHIUM HEXAMETHYLDISILAZIDE, 95%

Product Code: SIL6467.0

Cas No: 4039-32-1

R&D quantities:

100 g
$136.00
25 g
$42.00
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.

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
  • Boiling Point: 114-6° / 1

    EINECS Number: 223-725-6

    Melting Point: 71-2°

    Molecular Weight: 167.33

    Alternative Name: LITHIUM BIS(TRIMETHYLSILYL)AMIDE

    HMIS Key: 3-3-1-X

    Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents

    Formula: C6H18LiNSi2

    Purity: 95%

    TSCA: TSCA

    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

    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.

    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.

    Additional Properties: Sterically-hindered strong base