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

Preparation

CAS No.93102-05-7
Chemical Name:N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
CBNumber:CB2715045
Molecular Formula:C13H23NOSi
Formula Weight:237.41
MOL File:93102-05-7.mol

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

Boiling point 76 °C0.3 mm Hg(lit.)
Density 0.928 g/mL at 25 °C(lit.)
refractive index n20/D 1.492(lit.)
Flash point 151 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Soluble in chloroform, ethyl acetate.
form Liquid
pka 7.29±0.50(Predicted)
color Clear colorless to light yellow
Specific Gravity 0.928
Sensitive Moisture & Light Sensitive
Hydrolytic Sensitivity 2: reacts with aqueous acid
BRN 4311216
InChIKey RPZAAFUKDPKTKP-UHFFFAOYSA-N
CAS DataBase Reference 93102-05-7(CAS DataBase Reference)
UNSPSC Code 12352116
NACRES NA.22

Safety

Hazard Codes :Xi
Risk Statements :36/37/38
Safety Statements :26-37/39
RIDADR :1993
WGK Germany :3
HazardClass :3
PackingGroup :Ⅲ
HS Code :29319090

NFPA 704:

	1
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319-H335
Precautionary statements P261-P264-P271-P280-P302+P352-P305+P351+P338

N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine Price More Price(7)

Brand: Sigma-Aldrich(India)
Product number: 420697
Product name : N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
Purity: 96%
Packaging: 5G
Price: ₹11463.68
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 420697
Product name : N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
Purity: 96%
Packaging: 25G
Price: ₹35029.7
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 420697
Product name : N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
Purity: 96%
Packaging: 100G
Price: ₹108185.05
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: B1938
Product name : N-Benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine
Purity:
Packaging: 5G
Price: ₹6300
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: B1938
Product name : N-Benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine
Purity:
Packaging: 25G
Price: ₹22900
Updated: 2022/05/26
Buy: Buy

N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine Chemical Properties,Usage,Production

Preparation
N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine is most conveniently prepared by treatment of benzylamine with chloromethyltrimethylsilane followed by formaldehyde and methanol. Access to higher ether homologs is achieved by replacing methanol with the appropriate alcohol. An alternate procedure involves alkylation of lithium N-benzyltrimethylsilymethylamide with methoxymethyl chloride.
Chemical Properties N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine is clear colorless to light yellow liquid
Physical properties bp 77–80°C/0.5 mmHg.
Uses N-Benzyl-N-(methoxymethyl)- N-trimethylsilylmethylamine (1) is a valuable reagent for in situ generation of the N-benzyl azomethine ylide (2). It is generally preferred over alternative silylmethylamine precursors6–8 because of ease of handling and use. The ylide (2) is most conveniently generated from (1) using a catalytic amount of trifluoroacetic acid as described by Achiwa.Alternative catalysts include LiF, TBAF,Me3SiOTf–CsF, or Me3SiI–CsF. Mechanistic studies provide evidence that the reactive intermediate generated from (1) with either CF3CO2H or F? is a 1,3-dipolar species. Reaction of (2) with alkenes provides an efficient convergent route to pyrrolidine derivatives. Alkynes afford 3-pyrrolines which can be converted into pyrroles.The ylide (2) reacts most readily with electron deficient alkenes and alkynes since this pairing results in a narrow dipole HOMO–dipolarophile LUMO energy gap.Examples of suitable dipolarophiles include unsaturated esters, ketones, imides,nitriles,and sulfones. Cycloaddition occurs with complete cis stereospecificity (eq 1) which is consistent with a concerted mechanism. Dipolarophiles containing an endocyclic double bond afford fused bicyclic pyrrolidines, whereas substrates with an exocyclic double bond provide access to spirocyclic systems.
Uses N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine is useful reagent in synthesizing N-benzyl substituted pyrrolidines by [3+2] cycloaddition to α,ßunsaturated esters.
Uses N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine forms azomethine ylides which readily undergo [3+2] cycloaddition to α,?-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.
Preparation most conveniently prepared by treatment of benzylamine with chloromethyltrimethylsilane followed by formaldehyde and methanol.Access to higher ether homologs is achieved by replacing methanol with the appropriate alcohol. An alternate procedure involves alkylation of lithium N-benzyltrimethylsilymethylamide with methoxymethyl chloride.