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Boiling Point: 126-7°
EINECS Number: 213-668-5
Melting Point: <-76°
Molecular Weight: 161.39
Alternative Name: HMDS
Specific Gravity: 0.7742
Flashpoint: 12°C (54°F)
HMIS Key: 2-4-1-X
Hydrolytic Sensitivity: 7: reacts slowly with moisture/water
Refractive Index: 1.4080
Application: Review of synthetic utility.1
Review on organosilane protecting groups.2
Converts acid chlorides and alcohols to amines in a three-component reaction.3
Reacts with formamide and ketones to form pyrimidines.4
Lithium reagent reacts w/ aryl chlorides or bromides to provide primary anilines.5
Used to convert ketones to ?-aminophosphonates.6
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. 317-319.
2. Larson, G. L. “Silicon-Based Blocking Agents” Gelest, Inc. 2014.
3. Li, H.-H. et al. Eur. J. Org. Chem. 2008, 3623.
4. Tyagarajan, S.; Chakravarty, P. K. Tetrahedron Lett. 2005, 46, 7889.
5. Lee, S.; Jorgensen, M.; Hartwig, J. F. Org. Lett. 2001, 3, 2729.
6. Heo, Y. et al. Tetrahedron Lett. 2012, 53, 3897.
Fieser: F&F: Vol. 1, p 427; Vol. 2, p 159; Vol. 5, p 323; Vol. 6, p 273; Vol. 7, p 167; Vol. 8, p 29; Vol. 9, p 234; Vol. 11, p 38; Vol. 12, p 239; Vol. 13, p 141; Vol. 14, p 300.
Additional Properties: 325Ea, reaction w/SiO2 surface: 17.6 kcal/moleSpecific wetting surface: 485 m2/g?Hcomb: 6,052 kcal/mole?Hvap: 8.3 kcal molepKa: 7.55Dipole moment: 0.37 debyeDielectric constant: 1000 Hz: 2.27Surface tension: 18.2 mN/mVersatile silylation reagent; creates hydrophobic surfacesVapor pressure, 50°: 50 mm