111-74-0

Usage

Uses

Used in Pharmaceutical Industry:
N,N'-Diethylethylenediamine serves as a pharmaceutical intermediate, playing a crucial role in the synthesis of various drugs such as procainamide hydrochloride, tiapride, and cinchocaine. Its ability to form coordination complexes with metal ions aids in the development of these medicinal compounds, enhancing their therapeutic properties and effectiveness.
Used in Analytical Chemistry:
In the field of analytical chemistry, N,N'-Diethylethylenediamine is employed as an internal standard in liquid chromatographic methods. Specifically, it is used for checking the assay of ethambutol, a first-line antibiotic used in the treatment of tuberculosis. Its consistent and reliable performance as an internal standard ensures accurate and precise measurements in pharmaceutical analysis.
Used in Solvation Applications:
N,N'-Diethylethylenediamine is utilized for the solvation of lithium hexamethyldisilazide, a compound used in various chemical reactions and processes. Its ability to dissolve and stabilize N,N'-Diethylethylenediamine makes it a valuable solvent in certain chemical applications.
Used in Coordination Chemistry:
As a ligand, N,N'-Diethylethylenediamine forms coordination complexes with metal ions, such as trans-diaquabis(N,N'-diethylethylenediamine)nickel(II) chloride and copper(II)-N,N-Diethylethylenediamine. These complexes exhibit unique properties, including thermochromism, which is the change in color with temperature. This characteristic makes these complexes useful in various applications, such as temperature-sensitive materials and sensors.

Upstream product

• 871-78-3 N,N'-diacetylethylenediamine 
• 75-04-7 ethylamine 
• 106-93-4 ethylene dibromide 
• 75-03-6 ethyl iodide 
• 107-15-3 ethylenediamine 
• 75-07-0 acetaldehyde 
• 74-85-1 ethene 
• 107-06-2 1,2-dichloro-ethane 
• 150-77-6 N,N,N',N'-Tetraethylethylenediamine 
• 64-17-5 ethanol 
• 102600-38-4 N,N-diethyl-N,N'-ethanediyl-bis-toluene-4-sulfonamide 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 50-99-7 D-glucose 

Downstream Products

• 40424-21-3 1,3-diethyl-imidazolidin-2-one 
• 73941-41-0 1,3-diethyl-2-phenyl-imidazolidine 
• 56252-82-5 N-(2-diethylamino-ethyl)-palmitamide 
• 133146-52-8 N-Ethyl-N-(2-ethylamino-ethyl)-N'-trityl-propane-1,3-diamine 
• 133146-49-3 N-Ethyl-N-(2-{ethyl-[3-(trityl-amino)-propyl]-amino}-ethyl)-N'-trityl-propane-1,3-diamine 
• 6317-27-7 p-chlorophenyl mesylate 
• 90749-73-8 N-benzhydryl N,N'-diethylethylenediamine 
• 177898-48-5 1-{(2R,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[ethyl-(2-ethylamino-ethyl)-amino]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 179329-16-9 N-benzyl-N,N'-diethylethylenediamine 
• 179328-88-2 N,N'-Diethyl-N-[4-(4-methyl-piperazin-1-yl)-benzyl]-ethane-1,2-diamine 
• 179328-89-3 N,N'-Diethyl-N-[4-(4-ethyl-piperazin-1-yl)-benzyl]-ethane-1,2-diamine 
• 179328-91-7 N,N'-Diethyl-N-[4-(4-isopropyl-piperazin-1-yl)-benzyl]-ethane-1,2-diamine 
• 179328-90-6 N,N'-Diethyl-N-[4-(4-propyl-piperazin-1-yl)-benzyl]-ethane-1,2-diamine 

Relevant academic research and scientific papers

Low-Temperature Reductive Aminolysis of Carbohydrates to Diamines and Aminoalcohols by Heterogeneous Catalysis

Short amines, such as ethanolamines and ethylenediamines, are important compounds in today's bulk and fine chemicals industry. Unfortunately, current industrial manufacture of these chemicals relies on fossil resources and requires rigorous safety measures when handling explosive or toxic intermediates. Inspired by the elegant working mechanism of aldolase enzymes, a novel heterogeneously catalyzed process—reductive aminolysis—was developed for the efficient production of short amines from carbohydrates at low temperature. High-value bio-based amines containing a bio-derived C2 carbon backbone were synthesized in one step with yields up to 87 C%, in the absence of a solvent and at a temperature below 405 K. A wide variety of available primary and secondary alkyl- and alkanolamines can be reacted with the carbohydrate to form the corresponding C2-diamine. The presented reductive aminolysis is therefore a promising strategy for sustainable synthesis of short, acyclic, bio-based amines.

Experimental and Theoretical Study of an Intramolecular CF3-Group Shift in the Reactions of α-Bromoenones with 1,2-Diamines

The reactions of trifluoromethylated 2-bromoenones and N,N′-dialkyl-1,2-diamines have been studied. Depending on the structures of the starting compounds, the formation of 2-trifluoroacetylpiperazine or 3-trifluoromethylpiperazine-2-ones was observed. The mechanism of the reaction is discussed in terms of multistep processes involving sequential substitution of bromine in the starting α-bromoenones and intramolecular cyclization of the captodative aminoenones as key intermediates to form the target heterocycles. The results of theoretical calculations are in perfect agreement with the experimental data. The unique role of the trifluoromethyl group in this reaction is demonstrated.

Arylation of amines and monoarylation of symmetrical diamines in the presence of brine solution with diheteroaryl halides

A simple, scalable, ligand-free, and metal-free protocol for arylation of amines and monoarylation of symmetrical diamines with diheteroaryl halides in the presence of brine solution has been developed. The protocol has broad structural applicability for chemoselective monoarylation of a wide variety of symmetrical, cyclic, and acyclic aliphatic diamines. The protocol is also applicable for selective arylation of aliphatic amine in the presence of aromatic amine.

Nitric oxide reactivity of copper(ii) complexes of bidentate amine ligands: Effect of substitution on ligand nitrosation

Three copper(ii) complexes with bidentate ligands L1, L 2 and L3 [L1, N,N/- dimethylethylenediamine; L2, N,N/-diethylethylenediamine and L3, N,N/-diisobutylethylenediamine], respectively, were synthesized as their perchlorate salts. The single crystal structures for all the complexes were determined. The nitric oxide reactivity of the complexes was studied in acetonitrile solvent. The formation of thermally unstable [CuII-NO] intermediate on reaction of the complexes with nitric oxide in acetonitrile solution was observed prior to the reduction of copper(ii) centres to copper(i). The reduction was found to result with a simultaneous mono- and di-nitrosation at the secondary amine sites of the ligand. All the nitrosation products were isolated and characterized. The ratio of the yield of mono- and di-nitrosation product was found to be dependent on the N-substitution present in the ligand framework.

METHOD FOR PRODUCING N-MONOALKYL-SUBSTITUTED ALKYLENE AMINE

PROBLEM TO BE SOLVED: To provide a method for producing an N-monoalkyl-substituted alkylene amine especially useful for uses such as medicine intermediates, agrochemical intermediates, urethane resin-foaming catalysts, surfactants and the like among alkyl-substituted alkylene amine compounds from an alcohol and an alkylene amine as raw materials. SOLUTION: This method for producing the N-monoalkyl-substituted alkylene amine is characterized by reacting the alkylene amine with a ≥2C alkyl alcohol in the presence of a copper-containing oxide catalyst system. The N-monoalkyl-substituted alkylenamine is produced in high conversion and in N-monoalkylation selectivity.

Reaction of 1,2-dibromoethane with primary amines: Formation of N,N′-disubstituted ethylenediamines RNH-CH2CH2-NHR and homologous polyamines RNH-[CH2CH2NR]n-H

The reaction of primary amines RNH2 (R: Me, Et, iPr, tBu and Ph) with 1,2-dibromoethane gave N,N′-disubstituted ethylenediamines R-NH-CH2CH2-NH-R (1) in yields ranging from 10% (1a; R=Me) to 70% (1d, R=tBu; 1e, R=Ph). Pipe

Method and apparatus for sunless tanning

Apparatus for simulating skin tanning comprises a receptacle containing a fluid comprising dihydroxyacetone, a receptacle containing a fluid comprising a secondary polyamine, and dispensing means for simultaneously or sequentially providing desired amounts of dihydroxyacetone and polyamine.

Anodic Oxidation of Amines. VIII. Oxidation of Ethane-1,2-diamines

Anodic oxidation of ethylenediamines (ethane-1,2-diamines) was investigated by cyclic voltammetry and controlled potential electrolysis in aqueous carbonate buffer (pH 10) at a glassy-carbon electrode.The first wave of the diamines is developed at a lower potential than that of the corresponding β-alkanolamines.Among the oxidative bond cleavages, the relative amount of (α)C-(β)C bond fission is larger than that observed for β-alkanolamines and oxidative deamination is only observed after the (α)C-(β)C bond fission.A scheme for the reaction processes is proposed.Keywords: ethane-1,2-diamine; anodic oxidation; (α)C-(β)C bond fission; C-N bond fission; carbonate buffer; glassy-carbon electrode.