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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.
Isopropenoxytrimethylsilane; IPOTMS; 2-(Trimethylsiloxy)propene trimethyl[(1-methylvinyl)oxy]silane
Boiling Point: 94-5°
EINECS Number: 217-393-1
Molecular Weight: 130.26
Alternative Name: 2-(TRIMETHYLSILOXY)PROPENE
Specific Gravity: 0.786
Flashpoint: -1°C (30°F)
HMIS Key: 2-4-1-X
Hydrolytic Sensitivity: 7: reacts slowly with moisture/water
Refractive Index: 1.3960
Application: Reagent for synthesis of cyclic-acetone ketals.1
This and other enol silyl ethers add enantioselectively to imines.2
Reference: 1. Larson, G. et al. J. Org. Chem. 1973, 38, 3935.
2. Fuji, A. et al. J. Am. Chem. Soc. 1999, 121, 5450.
Additional Properties: Contains hexamethyldisiloxane