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

Bezeichnung:N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine

CAS-Nr93102-05-7

Englisch Name:N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine

CBNumberCB2715045

SummenformelC13H23NOSi

Molgewicht237.41

MOL-Datei93102-05-7.mol

N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine physikalisch-chemischer Eigenschaften

Siedepunkt	76 °C0.3 mm Hg(lit.)
Dichte	0.928 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.492(lit.)
Flammpunkt	151 °F
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	Soluble in chloroform, ethyl acetate.
Aggregatzustand	Liquid
pka	7.29±0.50(Predicted)
Farbe	Clear colorless to light yellow
Wichte	0.928
Sensitive	Moisture & Light Sensitive
Hydrolytic Sensitivity	2: reacts with aqueous acid
BRN	4311216
InChIKey	RPZAAFUKDPKTKP-UHFFFAOYSA-N
CAS Datenbank	93102-05-7(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-37/39
RIDADR	1993
WGK Germany	3
HazardClass	3
PackingGroup	Ⅲ
HS Code	29319090

Gefahreninformationscode (GHS)

N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine is clear colorless to light yellow liquid
Physikalische Eigenschaften
bp 77–80°C/0.5 mmHg.
Verwenden
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.
Verwenden
N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine is useful reagent in synthesizing N-benzyl substituted pyrrolidines by [3+2] cycloaddition to α,ßunsaturated esters.
Verwenden
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.
synthetische
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.

N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine Upstream-Materialien And Downstream Produkte

N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

93102-05-7, N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine Verwandte Suche:

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