111-74-0

Basic information

• Product Name: N,N'-Diethylethylenediamine
• Synonyms: N,N'-ETHYLENEDIETHYLDIAMINE;1,2-BIS(ETHYLAMINO)ETHANE;3,6-Diazaoctane;DEEN;N,N'-Diethylethylenediamine;1,2-Ethanediamine, N1,N2-diethyl-;Ai3-26637;Einecs 203-902-4
• CAS NO: 111-74-0
• Molecular Formula: C₆H₁₆N₂
• Molecular Weight: 116.2
• EINECS: 203-902-4
• Product Categories: Polyamines;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 111-74-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: -7.15°C (estimate)
• Boiling Point: 152-154 °C(lit.)
• Flash Point: 92 °F
• Appearance: colorless to yellow liquid
• Density: 0.811 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4326(lit.)
• PKA: 11.17±0.19(Predicted)
• Water Solubility: Miscible with water.
• Stability: Stable. Flammable. Incompatible with acids, acid chlorides, acid anhydrides, strong oxidizing agents. Absorbs, and reacts with,
• CAS DataBase Reference: N,N'-Diethylethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Diethylethylenediamine(111-74-0)
• EPA Substance Registry System: N,N'-Diethylethylenediamine(111-74-0)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 16-26-27-36/37/39-45
• RIDADR: UN 2685 8/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 111-74-0(Hazardous Substances Data)

Usage

Chemical Properties

liquid

Uses

N,N'-Diethylethylenediamine is used as an internal standard in liquid chromatographic method used for checking the assay of ethambutol. It is utilized for the solvation of lithium hexamethyldisilazide. It acts as a ligand and form coordination complexes such as trans-diaquabis(N,N'-diethylethylenediamine)nickel(II) chloride and copper(II)-N,N-Diethylethylenediamine, which shows thermochromic properties. Further, it is used as a pharmaceutical intermediate used in the synthesis of procainamide hydrochloride, tiapride and cinchocaine.

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 
• 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 
• 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 
• 179328-87-1 4-(4-{[Ethyl-(2-ethylamino-ethyl)-amino]-methyl}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

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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.

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.