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Product Code: SIT8588.5

Cas No: 76513-69-4

25 g
5 g
15 kg
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2 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

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
  • Hydroxyl group protecting unit
  • Deprotected with fluoride ion
  • Used to protect carboxylic acids
  • Protects anomeric center of pyranosides
  • Used for the introduction of hydroxymethyl group
  • Nafion SAC-13 has been shown to be a recyclable catalyst for the trimethylsilylation of primary, secondary, and tertiary alcohols in excellent yields and short reaction times
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure
  • 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

    Formula: C6H15ClOSi

    Purity: 95%

    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