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N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine, 94%
CAS: 93102-05-7 | C13H23NOSi | 237.418 g/mol
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Catalog number L19412.03
also known as L19412-03
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1 g
Price (EUR)
34,77
Online Exclusive
40,90Save 6,13 (15%)
Each
Chemical Identifiers
CAS93102-05-7
IUPAC Namebenzyl(methoxymethyl)[(trimethylsilyl)methyl]amine
Molecular FormulaC13H23NOSi
InChI KeyRPZAAFUKDPKTKP-UHFFFAOYSA-N
SMILESCOCN(CC1=CC=CC=C1)C[Si](C)(C)C
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Specifications
Specification Sheet
Specification SheetAppearance (Color)Clear colorless to pale yellow
FormLiquid
Elemental Analysis≥92.5%
Identification (FTIR)Conforms
Refractive Index1.4885-1.4955 @ 20°C
N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine forms azomethine ylides which readily undergo [3+2] cycloaddition to α,β-unsaturated esters affording N-benzyl substituted pyrrolidines in good yields. It reacts with asymmetric 1,3-dipolar cycloadditions in the practical, large-scale synthesis of chiral pyrrolidines. It is used in the the synthesis of 3-carboxy-1-azabicyclo[2.2.1]heptane derivatives, an important class of physiologically active compounds.
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
N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine forms azomethine ylides which readily undergo [3+2] cycloaddition to α,ß-unsaturated esters affording N-benzyl substituted pyrrolidines in good yields. It reacts with asymmetric 1,3-dipolar cycloadditions in the practical, large-scale synthesis of chiral pyrrolidines. It is used in the the synthesis of 3-carboxy-1-azabicyclo[2.2.1]heptane derivatives, an important class of physiologically active compounds.
Solubility
Soluble in chloroform, ethyl acetate.
Notes
Moisture & Light Sensitive. Store away from oxidizing agents.
N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine forms azomethine ylides which readily undergo [3+2] cycloaddition to α,ß-unsaturated esters affording N-benzyl substituted pyrrolidines in good yields. It reacts with asymmetric 1,3-dipolar cycloadditions in the practical, large-scale synthesis of chiral pyrrolidines. It is used in the the synthesis of 3-carboxy-1-azabicyclo[2.2.1]heptane derivatives, an important class of physiologically active compounds.
Solubility
Soluble in chloroform, ethyl acetate.
Notes
Moisture & Light Sensitive. Store away from oxidizing agents.
RUO – Research Use Only
General References:
- A. Stephen K. Hashmi; Dominic Riedel; Matthias Rudolph; Frank Rominger; Thomas Oeser. Regioselective Formation of Saturated Abnormal NHC-Gold(I) Complexes by [3+2] Cycloaddition of Azomethine Ylides and Isonitrile Gold(I) Complexes. Org. Biomol. Chem.2012, 18, 3827-3830.
- Ultrasound treatment with LiF in acetonitrile generates an azomethine ylide which undergoes 1,3-dipolar cycloaddition to olefins to give pyrrolidine derivatives in good yield: J. Org. Chem., 52, 235 (1987). Also found use in the the synthesis of 3-carboxy-1-azabicyclo[2.2.1]heptane derivatives, an important class of physiologically active compounds: J. Org. Chem., 66, 2526 (2001).