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Boiling Point: 80°
EINECS Number: 220-672-0
Melting Point: -44°
Molecular Weight: 153.09
Alternative Name: BROMOTRIMETHYLSILANE
Specific Gravity: 1.1725
Flashpoint: -3°C (27°F)
HMIS Key: 3-4-2-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Refractive Index: 1.422
Application: Review of synthetic utility.1
Converts acid chlorides to acid bromides.2
Deesterifies phosphorus esters.3
Converts nitroalkanes to nitroalkenes.4
Catalyzes the cross-coupling of heteroaromatics.5
Used in the synthesis of unsymmetrical phosphine oxides.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. 92-100.
2. Schmidt, A. H. et al. Synthesis 1981, 216.
3. Chovinard, P. M.; Bartlett, P. A. J. Org. Chem. 1986, 51, 75.
4. Kunetsky, R. A. et al. Tetrahedron Lett. 2005, 46, 5203.
5. Kita, Y. et al. J. Am. Chem. Soc. 2009, 131, 1668.
6. Fougére, C. et al. Eur. J. Org. Chem. 2009, 6048.
Fieser: F&F: Vol. 9, p 73; Vol. 10, p 59; Vol. 11, p 59; Vol. 12, p 799; Vol. 15, p 51; Vol. 16, p 50; Vol. 18, p 380; Vol. 19, p 373; Vol. 20, p 404.
Additional Properties: Dipole moment: 2.34 debyeIonization potential: 10.24 eV?Hform: -70.3 kcal/mole?Hvap: 30.8 kj/mole