106-58-1

Usage

Chemical Properties

clear colorless to yellow liquid

Uses

Catalyst for polyurethane foams and intermediate for cationic surfactants.

Synthesis Reference(s)

Canadian Journal of Chemistry, 63, p. 725, 1985 DOI: 10.1139/v85-120

Flammability and Explosibility

Flammable

Upstream product

• 110-85-0 piperazine 
• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 106-57-0 Glycine anhydride 
• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 140-31-8 aminoethylpiperazine 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 107-06-2 1,2-dichloro-ethane 
• 694-55-3 N-methyl-3,4-didehydropiperidine 
• 1184-78-7 trimethylamine-N-oxide 
• 7560-85-2 methyl 4-methylpiperazine-1-carboxylate 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 111-42-2 2,2'-iminobis[ethanol] 
• 74-89-5 methylamine 

Downstream Products

• 24996-75-6 1,1,4,4-tetramethylpiperazinium dibromide 
• 5450-74-8 1,4-dimethyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium dibromide 
• 6952-20-1 N,N,N',N'-Tetramethylpiperazinium diiodide 
• 35190-65-9 N,N-dimethylpiperazine dioxide 
• 50-00-0 formaldehyd 
• 140-79-4 N,N'-dinitrosopiperazine 
• 35190-65-9 trans-1,4-dimethylpiperazine 1,4-dioxide 
• 35190-65-9 1,4-Dimethyl-piperazine 1,4-dioxide 
• 83199-77-3 4-anilino-6-chloro-2-(N-methylpiperazino)-5-(methylthio)pyrimidine 
• 84708-07-6 [6-Chloro-2-(4-methyl-piperazin-1-yl)-5-methylsulfanyl-pyrimidin-4-yl]-cyclohexyl-amine 
• 102396-32-7 Benzyl-[6-chloro-2-(4-methyl-piperazin-1-yl)-5-methylsulfanyl-pyrimidin-4-yl]-amine 
• 102396-33-8 [6-Chloro-2-(4-methyl-piperazin-1-yl)-5-methylsulfanyl-pyrimidin-4-yl]-phenethyl-amine 
• 122596-11-6 1,1,4,4-tetramethyl-piperazinediium; bis-(toluene-4-sulfonate) 
• 101927-55-3 N-benzyl-4-(tert-butyl)benzamide 

Relevant academic research and scientific papers

Intermolecular cyclization of diethanolamine and methylamine to N,N′-dimethylpiperazine over zeolites under high pressure

Synthesis of N,N′-dimethylpiperazine via intermolecular cyclization of diethanolamine and methylamine has been investigated under high pressure conditions using zeolites and montmorillonite K10 for the first time. The HZSM-5(30) is particularly effective

Continuous N-alkylation reactions of amino alcohols using γ-Al2O3 and supercritical CO2: Unexpected formation of cyclic ureas and urethanes by reaction with CO2

The use of γ-Al2O3 as a heterogeneous catalyst in scCO2 has been successfully applied to the amination of alcohols for the synthesis of N-alkylated heterocycles. The optimal reaction conditions (temperature and substrate flow rate) were determined using an automated self-optimising reactor, resulting in moderate to high yields of the target products. Carrying out the reaction in scCO2 was shown to be beneficial, as higher yields were obtained in the presence of CO2 than in its absence. A surprising discovery is that, in addition to cyclic amines, cyclic ureas and urethanes could be synthesised by incorporation of CO2 from the supercritical solvent into the product.

N-methylation of nitrogen-containing heterocycles with dimethyl carbonate

Reactivity of dimethyl carbonate, the environmentally friendly reagent, as methylating agent for nitrogen-containing heterocyclic compounds has been studied. Reactions of imidazole, pyrazole, pyrrole, morpholine, and piperazine with dimethyl carbonate to afford N-methylated products were reported. The reactions were carried out with neither catalyst nor solvent at a temperature range of 110-170°C under atmospheric pressure. Copyright Taylor & Francis, Inc.

An enthalpic scale of hydrogen-bond basicity. 3. Ammonia, primary, secondary, and tertiary amines

A reliable enthalpic scale of hydrogen-bond acceptor strength (basicity) is built for aliphatic amines by means of a new infrared method, from the temperature variation of hydrogen-bond equilibrium constants. Enthalpies of hydrogen bonding to a reference hydrogen-bond acceptor, 4-fluorophenol, have been determined in CCl4 and/or C2C14 for ammonia and 68 primary, secondary, and tertiary amines. The scale spans from -23.8 kJ mol -1 for i-Pr2NCH(Et)2 to -39.4 kJ mol -1 for Et3N. This large variation is mainly explained by the basicity-enhancing electronic effects of alkyl groups, which can be overcompensated by dramatic basicity-decreasing steric effects. Relationships between ΔH° and the change in electronic energy or the infrared shift of the OH stretching upon hydrogen bonding are studied and found useful in the prediction of the hydrogen bond enthalpies of amines with several hydrogen-bond acceptor sites. A careful statistical analysis of the enthalpy-entropy relationship shows an isoentropic tendency. The entropies of 65% of hydrogen-bonding reactions between aliphatic amines and 4-fluorophenol have a mean value of -55.1 ± 4.2 J K-1 mol-1. Amines excluded from the isoentropic set are mainly severely hindered ones. The hydrogen-bond enthalpic scale can be useful in measuring the electrostatic character of Lewis bases.

A METHOD FOR THE ALKYLATION OF AMINES

The present invention pertains to a method for the alkylation of amines. In particular, the present invention relates to a method for preparing N, N, N', N , N -pentamethyldiethylenetriamine by reacting diethylenetriamine with methanol in the presence of hydrogen and a metal catalyst.

A METHOD FOR PREPARING ALKYLATED AMINES

The present invention pertains to a method for preparing an alkylated amine by reacting a primary or secondary amine with an alcohol in the presence of hydrogen, a metal catalyst supported by photosensitive titanium oxide, and UV irradiation. Advantageously, the reaction can be carried out under mild reaction conditions.

Method for synthesizing N-methyl fatty amine

The invention discloses a method N - for synthesizing,methyl fatty amine with fatty amine and methanol as a raw material, to catalyze N - methylation reaction. by using a transition metal iridium catalyst as a solvent, to avoid using the organic agent; to react and only generate water as a byproduct, without environmental hazard; and has wide application prospects.

N-Methylation of Amines with Methanol in Aqueous Solution Catalyzed by a Water-Soluble Metal-Ligand Bifunctional Dinuclear Iridium Catalyst

The N-methylation of amines with methanol in aqueous solution was proposed and accomplished by using a water-soluble metal-ligand bifunctional dinuclear iridium catalyst. In the presence of [(Cp*IrCl)2(thbpym)][Cl]2 (1 mol %), a range of desirable products were obtained in high yields under environmentally benign conditions. Notably, this research exhibited the potential of transition metal-catalyzed activation of methanol as a C1 source for the construction of the C-N bond in aqueous solution.

Electroactivated alkylation of amines with alcohols: Via both direct and indirect borrowing hydrogen mechanisms

A green, efficient N-alkylation of amines with simple alcohols has been achieved in aqueous solution via an electrochemical version of the so-called "borrowing hydrogen methodology". Catalyzed by Ru on activated carbon cloth (Ru/ACC), the reaction works well with methanol, and with primary and secondary alcohols. Alkylation can be accomplished by either of two different electrocatalytic processes: (1) in an undivided cell, alcohol (present in excess) is oxidized at the Ru/ACC anode; the aldehyde or ketone product condenses with the amine; and the resulting imine is reduced at an ACC cathode, combining with protons released by the oxidation. This process consumes stoichiometric quantities of current. (2) In a membrane-divided cell, the current-activated Ru/ACC cathode effects direct C-H activation of the alcohol; the resulting carbonyl species, either free or still surface-adsorbed, condenses with amine to form imine and is reduced as in (1). These alcohol activation processes can alkylate primary and secondary aliphatic amines, as well as ammonia itself at 25-70 °C and ambient pressure.

UiO-type metal-organic frameworks with NHC or metal-NHC functionalities for: N-methylation using CO2 as the carbon source

We demonstrate the first metal-organic framework (MOF) that catalyzes N-methylation of amines using 1 atm CO2 and phenylsilane under ambient conditions. Compared with its homogeneous analog, the incorporation of N-heterocyclic carbene (NHC) into the MOF provides more efficient catalysis with improved reaction kinetics, turnover numbers and recyclability. Moreover, the metalated NHC functionalized MOF achieves direct N-methylation of amines bearing carboxylate moieties, which are common building blocks in pharmaceutical chemistry.