benzyl(methoxymethyl)[(trimethylsilyl)methyl]amine

• ChemBase ID: 68425
• Molecular Formular: C13H23NOSi
• Molecular Mass: 237.41332
• Monoisotopic Mass: 237.15489089
• SMILES: N(Cc1ccccc1)(C[Si](C)(C)C)COC
• Canonical SMILES: COCN(C[Si](C)(C)C)Cc1ccccc1
• InChI: InChI=1S/C13H23NOSi/c1-15-11-14(12-16(2,3)4)10-13-8-6-5-7-9-13/h5-9H,10-12H2,1-4H3
• InChIKey: RPZAAFUKDPKTKP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl(methoxymethyl)[(trimethylsilyl)methyl]amine
• IUPAC Traditional name: benzyl(methoxymethyl)[(trimethylsilyl)methyl]amine
• Synonyms: N-(Methoxymethyl)-N-(trimethylsilylmethyl)-benzylamine; N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine; benzyl(methoxymethyl)[(trimethylsilyl)methyl]amine; N-Benzyl-1-Methoxy-N-((triMethylsilyl)Methyl)MethanaMine; N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine; N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine; N-(甲氧基甲基)-N-(三甲基硅烷基甲基)苄胺; N-甲氧基甲基-N-(三甲基硅烷)苄基胺

Database IDs

• CAS Number: 93102-05-7
• EC Number: 000-000-0
• MDL Number: MFCD00674005
• Beilstein Number: 4311216
• PubChem SID: 162034156; 24866346
• PubChem CID: 353442

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.6691823
• LogD (pH = 7.4): 3.472904
• Log P: 4.3118
• Molar Refractivity: 65.825 cm^3
• Polarizability: 28.38611 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 76 °C/0.3 mmHg(lit.); 76°C/0.3mm
• Flash Point: 150.8 °F; 66 °C; 66°C(150°F)
• Density: 0.928; 0.928 g/mL at 25 °C(lit.)
• Refractive Index: 1.4920; n20/D 1.492(lit.)
• Hydrophobicity(logP): 3.602

Safety Information

• Storage Warning: IRRITANT; Moisture & Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H227
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 90+%; 92%; 94%; 95%; 96%; 97%
• Linear Formula: C6H5CH2N(CH2OCH3)CH2Si(CH3)3

DETAILS

Sigma Aldrich - 420697

Application
Forms azomethine ylides which readily undergo [3+2] cycloaddition to α,β-unsaturated esters affording N-benzyl substituted pyrrolidines in good yields.1
Reacted in asymmetric 1,3-dipolar cycloadditions in the practical, large-scale synthesis of chiral pyrrolidines.
Packaging
1, 5, 25, 100 g in glass bottle

REFERENCES

• 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).