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2-(TRIMETHYLSILYL)ETHOXYMETHYL CHLORIDE, 95%
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.
2-(Trimethylsilyl)ethoxymethylchloride; SEM-chloride; Chloromethyl trimethylsilylethyl ether silane; [2-(Chloromethoxy)ethyl]trimethyl[2-[(chloromethyl)oxy]ethyl]trimethylsilane; 2-Chloromethyl 2-(trimethylsilyl)ethyl ether; SEM-Cl
EINECS Number: 278-483-4
Alternative Name: SEM-CHLORIDE
Specific Gravity: 0.942
Flashpoint: 46°C (115°F)
HMIS Key: 4-3-1-X
Hydrolytic Sensitivity: 7: reacts slowly with moisture/water
Refractive Index: 1.4350
Application: Review of synthetic utility.1
Hydroxyl group protection reagent, cleaved with fluoride.2
Useful in the introduction of a protected hydroxymethyl moiety.3
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. 628-632.
2. Lipshutz, B. et al. Tetrahedron Lett. 1980, 21, 3343.
3. Eichelberger, U. et al. Tetrahedron 2002, 58, 545.
Fieser: F&F: Vol. 10, p 431; Vol. 15, p 344; Vol. 16, p 361.
Additional Properties: Stabilized with iPr2MeN