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420697

Sigma-Aldrich

N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine

96%

Synonym(s):

N-(Methoxymethyl)-N-(trimethylsilylmethyl)-N-benzylamine, N-Benzyl-N-(methoxymethyl)trimethylsilylmethylamine, Benzyl(methoxymethyl)[(trimethylsilyl)methyl]amine

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About This Item

Linear Formula:
C6H5CH2N(CH2OCH3)CH2Si(CH3)3
CAS Number:
Molecular Weight:
237.41
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

96%

form

liquid

refractive index

n20/D 1.492 (lit.)

bp

76 °C/0.3 mmHg (lit.)

density

0.928 g/mL at 25 °C (lit.)

SMILES string

COCN(Cc1ccccc1)C[Si](C)(C)C

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

InChI key

RPZAAFUKDPKTKP-UHFFFAOYSA-N

Application

Forms azomethine ylides which readily undergo [3+2] cycloaddition to α,ß-unsaturated esters affording N-benzyl substituted pyrrolidines in good yields.
Reacted in asymmetric 1,3-dipolar cycloadditions in the practical, large-scale synthesis of chiral pyrrolidines.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

150.8 °F

flash_point_c

66 °C

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


Certificates of Analysis (COA)

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Synthesis, 2646-2646 (2006)
Kotian, Pravin L.; et al.
Organic Process Research & Development, 9(2), 193-197 (2005)

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