ETHYL (2-TRIMETHYLSILYL)ACETATE

Product Code: SIE4901.6
CAS No: 4071-88-9
SDS Sheets: EU | US
Pack Size
Quantity
Price
 
5 g
$66.00

Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    223-783-2
  • HMIS

    2-3-0-X
  • Molecular Formula

    C7H16O2Si
  • Molecular Weight (g/mol)

    160.29
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    157-158
  • Density (g/mL)

    0.876
  • Flash Point (˚C)

    35 °C
  • Refractive Index @ 20˚C

    1.4149

Additional Properties

  • Hydrolytic Sensitivity

    2: reacts with aqueous acid
  • 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

    Fieser

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

    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.

    Safety

  • Packaging Under

    Nitrogen
  • 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