67990-20-9

Basic information

• Product Name: 1,1'-ethylenebis[3-methylpiperidine]
• Synonyms: 1,1'-ethylenebis[3-methylpiperidine];1,1'-(1,2-Ethanediyl)bis(3-methylpiperidine);Einecs 268-042-4;Piperidine, 1,1'-(1,2-ethanediyl)bis(3-methyl-
• CAS NO: 67990-20-9
• Molecular Formula: C14H28N2
• Molecular Weight: 224.38552
• EINECS: 268-042-4
• Mol File: 67990-20-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 278.6°Cat760mmHg
• Flash Point: 111.3°C
• Appearance: /
• Density: 0.902g/cm³
• CAS DataBase Reference: 1,1'-ethylenebis[3-methylpiperidine](CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-ethylenebis[3-methylpiperidine](67990-20-9)
• EPA Substance Registry System: 1,1'-ethylenebis[3-methylpiperidine](67990-20-9)

Safety Data

• Hazardous Substances Data: 67990-20-9(Hazardous Substances Data)

Usage

Chemical Class

Piperidines

Physical State

Colorless to pale yellow liquid

Odor

Faint amine-like

Applications

a. Corrosion inhibitor in oilfield applications
b. Stabilizer in the rubber industry
c. Intermediate in the production of dyes, pharmaceuticals, and other organic compounds

Solubility

Soluble in most organic solvents

Stability

Relatively stable under normal storage and handling conditions

Safety Precautions

a. Can cause skin and eye irritation
b. Can cause respiratory and digestive tract issues if inhaled or ingested

Hazardous Nature

Potential health risks if not handled properly

Upstream product

• 124-38-9 carbon dioxide 
• 626-56-2 3-Methylpiperidine 
• 106-93-4 ethylene dibromide 

Relevant articles and documents

Selective synthesis of formamides, 1,2-bis(N-heterocyclic)ethanes and methylamines from cyclic amines and CO2/H2 catalyzed by an ionic liquid-Pd/C system

The reduction of CO2 with amines and H2 generally produces N-formylated or N-methylated compounds over different catalysts. Herein, we report the selective synthesis of formamides, 1,2-bis(N-heterocyclic)ethanes, and methylamines, which is achieved over an ionic liquid (IL, e.g., 1-butyl-3-methylimidazolium tetrafluoroborate, [BMIm][BF4])-Pd/C catalytic system. By simply varying the reaction temperature, formamides and methylamines can be selectively produced, respectively, in high yields. Interestingly, 1,2-bis(N-heterocyclic)ethanes can also be obtained via the McMurry reaction of the formed formamide coupled with subsequent hydrogenation. It was found that [BMIm][BF4] can react with formamide to form a [BMIm]+-formamide adduct; thus combined with Pd/C it can catalyze McMurry coupling of formamide in the presence of H2 to afford 1,2-bis(N-heterocyclic)ethane. Moreover, Pd/C-[BMIm][BF4] can further catalyze the hydrogenolysis of 1,2-bis(N-heterocyclic)ethane to access methylamine. [BMIm][BF4]-Pd/C was tolerant to a wide substrate scope, giving the corresponding formamides, 1,2-bis(N-heterocyclic)ethanes or methylamines in moderate to high yields. This work develops a new route to produce N-methylamine and opens the way to produce 1,2-bis(N-heterocyclic)ethane from cyclic amine as well.

Gem-diamines as highly active organocatalysts for carbon-carbon bond formation

Diamines with neighbour nitrogen atoms have been used as base catalysts in the Knoevenagel condensation reaction between benzaldehyde and ethyl cyanoacetoacetate. The catalytic results show that a good basic catalyst requires a combination of two factors: high proton affinity and the ability to return the proton to the oxoanion intermediate. Computational chemistry calculations show this by characterizing the reactants, products, and transition states and by calculating the activation energies of the different reaction steps. A diamine, di(3-methylpiperidine)methane (B), has been found with a higher catalytic activity than DMAN despite its lower proton affinity, demonstrating that not only the proton affinity, but also the steric ability to abstract the protons, are important in explaining the catalytic results.