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Trimethylsilyl Blocking Agent
Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.
Trimethylbromosilane; Bromotrimethylsilane; Trimethylsilyl bromide; TMBS
EINECS Number: 220-672-0
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