4071-88-9

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ETHYL (2-TRIMETHYLSILYL)ACETATE

Product Code: SIE4901.6

Cas No: 4071-88-9

R&D quantities:

5 g
$55.00
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.

Ethyl trimethylsilylacetate; Ethyl(trimethylsilyl)acetate; (Trimethylsilyl)acetic acid ethyl ester; Acetic acid (trimethylsilyl)-, ethyl ester
  • Silylation of ketones, alcohols, acetylenes, thiols under the influence of fluoride ion
  • 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
  • Boiling Point: 157-8°

    EINECS Number: 223-783-2

    Molecular Weight: 160.29

    Specific Gravity: 0.876

    Flashpoint: 35°C (95°F)

    HMIS Key: 2-3-0-X

    Hydrolytic Sensitivity: 2: reacts with aqueous acid

    Formula: C7H16O2Si

    Refractive Index: 1.4149

    Application: Review of synthetic utility.1
    In combination with LDA converts ketones to ?,?-unsaturated esters.2
    Promotes the addition of alkylnitriles to imines.3
    Reagent for conversion of carboxylic acids to ?-hydroxyesters.4

    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. 297-299.
    2. Larson, G. L. et al. Synth. Commun. 1999, 20, 1095.
    3. Poisson, T. et al. J. Org. Chem. 2009, 74, 3516.
    4. Wadhwa, K.; Verkade, J. J. Org. Chem. 2009, 74, 4368.

    Fieser: F&F: Vol. 7, p 150; Vol. 11, p 234, p 237.