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TRIS(TRIMETHYLSILYL)PHOSPHINE, 10% in hexane
Specific Gravity: 0.72
Flashpoint: -23°C (-9°F)
HMIS Key: 4-4-2-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Application: Review of synthetic utility.1
In combination with indium acetate forms InP quantum dots.2,3
Promotes borylative dienylation/aldeyhyde coupling.4
Reaction with methyllithium gives lithium bis(trimethylsilyl)phosphide,5 which reacts with dialkylformamides to give functional phosphaalkenes.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. 422-427.
2. Bharal, D. et al. J. Am. Chem. Soc. 2005, 127, 11364.
3. Kim, S. et al. J. Am. Chem. Soc. 2005, 127, 10526.
4. Cho, H. Y.; Morken, J. P. J. Am. Chem. Soc. 2010, 132, 7576.
5. Askham, F. R. et al. J. Am. Chem. Soc. 1985, 107, 7423.
6. Prischenko, A. A. et al. Heteroatom. Chem. 2010, 21, 441.