Description
Additional Properties
Hydrolytic Sensitivity 7: reacts slowly with moisture/water 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 Fieser F&F: Vol. 3, p 317; Vol. 4, p 544; Vol. 6, p 634; Vol. 18, p 382. 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. 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. 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. Diethylaminotrimethy
lsilane; Trimethylsilyldiethy
lamine; N,N-Diethyl-1,1,1-tr
imethylsilylamine; N,N-Diethyl-1,1,1-tr
imethylsilylamine; 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
