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Product Code: SID3398.0

Cas No: 996-50-9

2 kg
100 g
25 g
14 kg
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150 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.

Alkyl Silane - Conventional Surface Bonding

Aliphatic, fluorinated aliphatic or substituted aromatic hydrocarbon substituents are the hydrophobic entities which enable silanes to induce surface hydrophobicity. The organic substitution of the silane must be non-polar. The hydrophobic effect of the organic substitution can be related to the free energy of transfer of hydrocarbon molecules from an aqueous phase to a homogeneous hydrocarbon phase. A successful hydrophobic coating must eliminate or mitigate hydrogen bonding and shield polar surfaces from interaction with water by creating a non-polar interphase. Although silane and silicone derived coatings are in general the most hydrophobic, they maintain a high degree of permeability to water vapor. This allows coatings to breathe and reduce deterioration at the coating interface associated with entrapped water. Since ions are not transported through non-polar silane and silicone coatings, they offer protection to composite structures ranging from pigmented coatings to rebar reinforced concrete. A selection guide for hydrophobic silanes can be found on pages 22-31 of the Hydrophobicity, Hydrophilicity and Silane Surface Modification brochure.

Diethylaminotrimethylsilane; Trimethylsilyldiethylamine; N,N-Diethyl-1,1,1-trimethylsilylamine; N,N-Diethyl-1,1,1-trimethylsilylamine; TMSDMEA
  • ΔHform: -367 kJ/mole
  • Silylation reagent
  • Reacts with benzynes and aldehydes to form O-aminobenzyl alcohols
  • Provides a convenient synthesis of enoltrimethylsilyl ethers
  • Releases diethylamine upon reaction
  • Moderately strong silylating agent
  • Selectively silylates equatorial over axial hydroxyls
  • 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: 213-637-6

    Alternative Name: TMSDEA

    Specific Gravity: 0.7627

    Flashpoint: 10°C (50°F)

    HMIS Key: 3-4-1-X

    Hydrolytic Sensitivity: 7: reacts slowly with moisture/water

    Formula: C7H19NSi


    Refractive Index: 1.4109

    Application: Review of synthetic utility.1
    Reacts with benzynes and aldehydes to form o-aminobenzyl alcohols.2
    Provides a convenient synthesis of enoltrimethylsilyl ethers.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. 598-599.
    2. Yoshida, H. et al. Org. Lett. 2007, 9, 3367.
    3. Yamamoto, Y.; Matui, C. Organometallics 1997, 16, 2204.

    Fieser: F&F: Vol. 3, p 317; Vol. 4, p 544; Vol. 6, p 634; Vol. 18, p 382.

    Additional Properties: ?Hform: -87.7 kcal/mole
    Silylation reagent