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Diethoxymethylsilane, 96%, Thermo Scientific Chemicals
化学物質識別子
CAS2031-62-1
IUPAC Namediethoxy(methyl)silyl
Molecular FormulaC5H13O2Si
InChI KeyGAURFLBIDLSLQU-UHFFFAOYSA-N
SMILESCCO[Si](C)OCC
さらに表示
仕様
スペックシート
スペックシートAppearance (Color)Clear colorless
FormLiquid
Assay (GC)≥95.0%
Identification (FTIR)Conforms
Refractive Index1.3730-1.3790 @ 20?C
Diethoxymethylsilane is used in the preparation of N,N'-methylsilanediyl-bis-phthalimide by reacting with phthalimide. It is used as a reagent in the selective reduction of carbonyl compounds, hydorosilylation of alkenes, tandem reductive aldol reaction and rhodium-catalyszed silylcarbocyclization.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Diethoxymethylsilane is used in the preparation of N,N′-methylsilanediyl-bis-phthalimide by reacting with phthalimide. It is used as a reagent in the selective reduction of carbonyl compounds, hydorosilylation of alkenes, tandem reductive aldol reaction and rhodium-catalyszed silylcarbocyclization.
Solubility
Miscible with water, 1,4-dioxane, tetrahydrofuran, acetonitrile, dichloromethane, chloroform, dimethyl sulfoxide, hexamethylphosphoric triamide and toluene. Insoluble in diethyl ether and hexane.
Notes
Incompatible with oxidizing agents, acids and bases.
Diethoxymethylsilane is used in the preparation of N,N′-methylsilanediyl-bis-phthalimide by reacting with phthalimide. It is used as a reagent in the selective reduction of carbonyl compounds, hydorosilylation of alkenes, tandem reductive aldol reaction and rhodium-catalyszed silylcarbocyclization.
Solubility
Miscible with water, 1,4-dioxane, tetrahydrofuran, acetonitrile, dichloromethane, chloroform, dimethyl sulfoxide, hexamethylphosphoric triamide and toluene. Insoluble in diethyl ether and hexane.
Notes
Incompatible with oxidizing agents, acids and bases.
RUO – Research Use Only
General References:
- Silane reducing agent; see Appendix 4. In the presence of KF or CsF, reduces aldehydes and ketones to alcohols (via the silyl ether): Tetrahedron, 37, 2165 (1981). With CsF, the reaction can be extended to esters: Synthesis, 558 (1981). Both reactions are improved in DMSO or DMF as solvent: Synthesis, 981 (1982).
- Hydosilylation of olefinic compounds can be effected, e.g. in the presence of PtO2: Org. Lett., 4, 2117 (2002).
- Niljianskul, N.; Zhu, S.; Buchwald, S. L. Enantioselective Synthesis of alfa-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes. Angew. Chem. 2015, 127 (5), 1658-1661.
- Wang, Y. M.; Bruno, N. C.; Placeres, A. L.; Zhu, S.; Buchwald, S. L. Enantioselective Synthesis of Carbo-and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach. J. Am. Chem. Soc. 2015, 137 (33), 10524-10527.