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Boiling Point: 157-8°
EINECS Number: 223-783-2
Molecular Weight: 160.29
Specific Gravity: 0.876
Flashpoint: 35°C (95°F)
HMIS Key: 2-3-0-X
Hydrolytic Sensitivity: 2: reacts with aqueous acid
Refractive Index: 1.4149
Application: Review of synthetic utility.1
In combination with LDA converts ketones to ?,?-unsaturated esters.2
Promotes the addition of alkylnitriles to imines.3
Reagent for conversion of carboxylic acids to ?-hydroxyesters.4
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. 297-299.
2. Larson, G. L. et al. Synth. Commun. 1999, 20, 1095.
3. Poisson, T. et al. J. Org. Chem. 2009, 74, 3516.
4. Wadhwa, K.; Verkade, J. J. Org. Chem. 2009, 74, 4368.
Fieser: F&F: Vol. 7, p 150; Vol. 11, p 234, p 237.