111-37-5

Basic information

• Product Name: N-ETHYL-N'-METHYLETHYLENEDIAMINE
• Synonyms: 1,2-Ethanediamine, N-ethyl-N'-methyl-;2,5-Diazaheptane;N-ETHYL-N'-METHYLETHYLENEDIAMINE;ethyl(2-(methylamino)ethyl)amine;N-Ethyl-N'-methyl-1,2-ethanediamine;N-Methyl-N'-ethyl-1,2-ethanediamine;N-ethyl-N'-methyl-ethane-1,2-diamine;N-ethyl-N'-methylethane-1,2-diamine
• CAS NO: 111-37-5
• Molecular Formula: C₅H₁₄N₂
• Molecular Weight: 102.18
• EINECS: 203-863-3
• Mol File: 111-37-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 100-103°C
• Flash Point: 8.7°C
• Appearance: /
• Density: 0.793g/cm³
• Vapor Pressure: 10.2mmHg at 25°C
• Refractive Index: 1.417
• PKA: 10.87±0.10(Predicted)
• CAS DataBase Reference: N-ETHYL-N'-METHYLETHYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ETHYL-N'-METHYLETHYLENEDIAMINE(111-37-5)
• EPA Substance Registry System: N-ETHYL-N'-METHYLETHYLENEDIAMINE(111-37-5)

Safety Data

• Hazardous Substances Data: 111-37-5(Hazardous Substances Data)

Usage

Uses

N-Ethyl-N''-methylethylenediamine is used as a reactant in the preparation of substituted indoles as PPAR-γ binding agents.

InChI:InChI=1/C5H14N2/c1-3-7-5-4-6-2/h6-7H,3-5H2,1-2H3

Upstream product

• 75-04-7 ethylamine 
• 32315-92-7 N-methyl-2-chloroethylamine 
• 4535-87-9 N-(2-chloroethyl)ethylamine hydrochloride 
• 74-89-5 methylamine 
• 444147-25-5 N-ethyl-N'-methyl-oxalamide 

Downstream Products

• 483303-58-8 6-benzyloxycarbonylamino-1-ethyl-4-methylhexahydro-1,4-diazepine 
• 483305-04-0 4-chloro-N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)-2-methoxy-5-sulfamoylbenzamide 
• 483305-03-9 4-(N-benzyl-N-methyl)amino-N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)-5-fluoro-2-methoxybenzamide 
• 483305-02-8 4-(N-benzyl-N-methyl)amino-2,5-difluoro-N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)benzamide 
• 129920-21-4 1-ethyl-2,3-dimethyl-1,3,2-diazaborolidine 
• 7550-35-8 lithium bromide 

Relevant articles and documents

Synthesis and structure-activity relationships of 4-amino-5-chloro-N-(1,4- dialkylhexahydro-1,4-diazepin-6-yl)-2-methoxybenzamide derivatives, novel and potent serotonin 5-HT3 and dopamine D2 receptors dual antagonist

In search of a dopamine D2 and serotonin 5-HT3 receptors dual antagonist as a potential broad antiemetic agent, a number of benzamides were prepared from 4-amino-5-chloro-2-methoxybenzoic acid derivatives and 6-amino-1,4-dialkylhexahydro-1,4-diazepines and evaluated for their binding affinity for the dopamine D2 and the serotonin 5-HT3 receptors using rat brain synaptic and rat cortical membranes, respectively. From the results of both in vitro receptor binding and in vivo biological assays for the dopamine D2 receptor, 1-ethyl-4-methylhexahydro-1,4- diazepine ring was selected as an optimum amine moiety. Introduction of one methyl group on the nitrogen atom at the 4-position and/or modification of the substituent at the 5-position of the 4-amino-5-chloro-2-methoxybenzoyl moiety caused a marked increase in the dopamine D2 receptor binding affinity along with a potent 5-HT3 receptor binding affinity. Among the compounds, 5-chloro-N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)-2-methoxy-4- methylaminobenzamide (82), 5-bromo (110), and 5-iodo (112) analogues exhibited a much higher affinity for the dopamine D2 receptor than that of metoclopramide (IC50=17.5-61.0 nM vs. 483 nM). In particular, 82 showed a potent antagonistic activity for both receptors in vivo tests. Optical resolution of the racemate 82 brought about a dramatic change in the pharmacological profile with the (R)-enantiomer exhibiting a strong affinity for both the dopamine D2 and the 5-HT3 receptors, while the corresponding (S)-enantiomer had a potent and selective serotonin 5-HT 3 receptor binding affinity.

Synthesis of 1,3-Disubstituted Diazolidines

Symmetrical and unsymmetrical 1,3-diaminoethanes 1 are obtained by the reduction of N,N'-disubstituted oxamides 4 with lithium aluminum hydride.The oxamides 4 are readily produced by treatment of diethyl oxalate with primary amines.The 1,3-diaminoethanes 1 lead to 1,3-diazolidines 2 on treatment with formaldehyde.