6974-95-4

Basic information

• Product Name: 4-[(1-methylpyrrol-2-yl)methyl]morpholine
• Synonyms: 4-[(1-methylpyrrol-2-yl)methyl]morpholine
• CAS NO: 6974-95-4
• Molecular Formula: C10H16N2O
• Molecular Weight: 0
• Mol File: 6974-95-4.mol

Chemical Properties

• Boiling Point: 271.8°C at 760 mmHg
• Flash Point: 118.2°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 0.00633mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 4-[(1-methylpyrrol-2-yl)methyl]morpholine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(1-methylpyrrol-2-yl)methyl]morpholine(6974-95-4)
• EPA Substance Registry System: 4-[(1-methylpyrrol-2-yl)methyl]morpholine(6974-95-4)

Safety Data

• Hazardous Substances Data: 6974-95-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H16N2O/c1-11-4-2-3-10(11)9-12-5-7-13-8-6-12/h2-4H,5-9H2,1H3

Upstream product

• 110-91-8 morpholine 
• 96-54-8 N-Methylpyrrole 
• 50-00-0 formaldehyd 
• 18811-63-7 N-(ethoxymethyl)morpholine 
• 5625-90-1 4-(morpholinomethyl)morpholine 

Relevant articles and documents

The activation of aminals and aminol ethers by sulfur dioxide and their reactions with electron rich aromatic compounds

Reactions of bis(dialkylamino)methanes and ethoxydialkylaminomethanes with nucleophilic aromatic heterocycles in the presence of sulfur dioxide result in the formation of the expected Mannich bases in good yields. Reactions of phenols are similarly activated by sulfur dioxide which lead to improved regioselectivity: in particular the reactions of 2,5-dimethylphenol result in the formation of 2-dialkylaminomethyl-3,6-dimethylphenol whereas reaction occurs at the I-position using the classical procedures.

The generation of iminium ions using chlorosilanes and their reactions with electron rich aromatic heterocycles

Dichlorodimethylsilane and trichloromethylsilane have been used to generate iminium ions from aminals and aminol ethers derived from secondary alkylamines, including glycine derivatives, in aprotic media which were shown to undergo reactions with electron rich aromatic heterocycles, including furan, to give mono-aminoalkylation products in good yields. Whereas chlorotrimethylsilane has been shown to generate iminium ions from aminol ethers, no evidence was adduced for the involvement of iminium ions using aminals. 2,5-Disubstitution of N-methylpyrrole was the major result in reactions of N-methylpyrrole with aminals in the presence of chlorotrimethylsilane where no build up of hydrogen chloride occurs and where chlorotrimethylsilane can function catalytically. Experimental results, including the use of bis(trimethylsilyl)acetamide as a proton scavenger, and some relative rate data, are presented that allow possible mechanisms to be evaluated.

MANNICH REACTIONS OF Π-EXCESSIVE HETEROCYLES USING BIS-(DIALKYLAMINO)METHANES AND ALKOXYDIALKYLAMINOMETHANES ACTIVATED WITH ACETYL CHLORIDE OR SULPHUR DIOXIDE

Π-Excessive heterocyles react rapidly with bis(dialkylamino)methanes (aminals) and alkoxydialkylaminomethanes (aminol ethers) in acetonitrile to afford Mannnich bases in good yields when ativated by means of an acidi reagent suh as acetyl chloride or sulphur dioxide: the principal ompound studied was N-methylpyrrole.