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LITHIUM HEXAMETHYLDISILAZIDE, 95%
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
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