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L19412 N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine, 94%

CAS Number
93102-05-7
Synonyms

Stock No. Size Price ($) Quantity Availability
L19412-03 1g 41.10
L19412-06 5g 128.00
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N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine, 94%

MDL
MFCD00674005
EINECS
000-000-0

Chemical Properties

Formula
C13H23NOSi
Formula Weight
237.42
Boiling Point
76°/0.3mm
Flash Point
66°(150°F)
Density
0.928
Refractive Index
1.4920
Storage & Sensitivity
Keep Cold. Moisture Sensitive. Light Sensitive. Store under Nitrogen.
Solubility
Soluble in chloroform, ethyl acetate.

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.

Notes

Moisture & Light Sensitive. Store away from oxidizing agents.

Literature 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).

GHS Hazard and Precautionary Statements

Hazard Statements: H227-H315-H319-H335

Combustible liquid. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P210-P235-P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
4311216
Harmonized Tariff Code
2931.90
TSCA
No

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