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Bridging Silicon-Based 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.
Di-tert-butyldichlorosilane; Bis(1,1-dimethylethyl)dichlorosilane; Dichlorobis(1,1-dimethylethyl)silane; DTBS
Boiling Point: 190-1°
EINECS Number: 242-273-0
Melting Point: -15°
Molecular Weight: 213.22
Specific Gravity: 1.009
Flashpoint: 61°C (142°F)
HMIS Key: 3-2-1-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Refractive Index: 1.4561
Application: Review of synthetic utility.1
Reagent for protection of 1,2 and 1,3 diols.2
Used as the source for di-tert-butylsilylene, in particular for the thermal silylene precursor, 1-silabicyclo[4.2.0]heptane.3 The silabicycloheptane di-tert-butylsilylene precursor has been utilized in a number of synthetic applications.4,5,6
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. 201-207.
2. Trost, B. et al. Tetrahedron Lett. 1981, 22, 4999.
3. Driver, T. G.; Franz, A. K.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 6524.
4. Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2004, 126, 9993.
5. Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2003, 125, 10659.
6. Howard, B. E.; Woerpel, K. A. Org. Lett. 2007, 9, 4651.