115287-37-1

Basic information

• Product Name: N-Methyl-N-(2-(4-nitrophenoxy)ethyl)-2-(4-nitrophenyl)ethanamine
• Synonyms: 4-NITROPHENYL-[5-(4-NITROPHENYL)-3-AZA-3-METHYLPENTYL]-ETHER;N-METHYL-[2-(4-NITROPHENOXY)ETHYL][2-(4-NITROPHENYL)ETHYL]-AMINE;N-METHYL-N-(2-(4-NITROPHENOXY)ETHYL)-2-(4-NITROPHENYL)ETHANAMINE;Benzeneethanamine,N-methyl-4-nitro-N-[2-(4-nitrop;Methyl-(4-nitrophenylethyl)-(4-nitrophenoxyethyl)amine;N-Methyl-4-nitro-N-[2-(4-nitrophenoxy)ethyl-benzeneethanamine;N-methyl-N-(2-(4-nitrophenoxy)ethyl)-2-(;N-METHYL-4-NITRO-N-[2-(4-NITROPHENOXY)ETHYL]PHENETHYLAMINE
• CAS NO: 115287-37-1
• Molecular Formula: C₁₇H₁₉N₃O₅
• Molecular Weight: 345.35
• Product Categories: Chemical Amines;Amines;Aromatics
• Mol File: 115287-37-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 70.0 to 74.0 °C
• Boiling Point: 513.2 °C at 760 mmHg
• Flash Point: 264.1 °C
• Appearance: brown solid
• Density: 1.273 g/cm³
• Vapor Pressure: 1.21E-10mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 7.60±0.50(Predicted)
• CAS DataBase Reference: N-Methyl-N-(2-(4-nitrophenoxy)ethyl)-2-(4-nitrophenyl)ethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-N-(2-(4-nitrophenoxy)ethyl)-2-(4-nitrophenyl)ethanamine(115287-37-1)
• EPA Substance Registry System: N-Methyl-N-(2-(4-nitrophenoxy)ethyl)-2-(4-nitrophenyl)ethanamine(115287-37-1)

Safety Data

• Hazardous Substances Data: 115287-37-1(Hazardous Substances Data)

Usage

Chemical Properties

Brown Solid

Uses

Methyl-(4-nitrophenylethyl)-(4-nitrophenoxyethyl)amine (cas# 115287-37-1) is a compound useful in organic synthesis.

InChI:InChI=1/C17H19N3O5/c1-18(11-10-14-2-4-15(5-3-14)19(21)22)12-13-25-17-8-6-16(7-9-17)20(23)24/h2-9H,10-13H2,1H3

Synthetic route

1-(2-chloroethoxy)-4-nitrobenzene (3383-72-0) + N-methyl-N-[2-(4-nitro-phenyl)-ethyl]-amine (85176-37-0) → 1-(4-nitrophenoxy)-2-ethane (115287-37-1)

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile for 72h; Heating;	64%
With sodium iodide; potassium carbonate In acetonitrile

1-(4-nitrophenoxy)-2-ethane (115287-37-1) → 1-(4-aminophenoxy)-2-[N-(4-aminophenethyl)-N-methylamino]ethane (115256-13-8)

Conditions	Yield
With palladium 10% on activated carbon In acetic acid butyl ester; ethyl acetate at 6℃; under 2250.23 Torr; for 60h; Solvent; Temperature; Pressure;	93.7%
With hydrogen; nickel In ethanol under 2280 Torr; for 16h; Ambient temperature;	72%
aluminum nickel In ethanol

1-(4-nitrophenoxy)-2-ethane (115287-37-1) → dofetilide (115256-11-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / H2 / Raney nickel / ethanol / 16 h / 2280 Torr / Ambient temperature 2: 51 percent / CH2Cl2 / Ambient temperature View Scheme

Upstream product

• 3383-72-0 1-(2-chloroethoxy)-4-nitrobenzene 
• 85176-37-0 N-methyl-N-[2-(4-nitro-phenyl)-ethyl]-amine 

Downstream Products

• 115256-11-6 dofetilide 
• 115256-13-8 1-(4-aminophenoxy)-2-[N-(4-aminophenethyl)-N-methylamino]ethane 

Relevant articles and documents

Selective class III antiarrhythmic agents. 1. Bis(arylalkyl)amines

A series of bis(arylalkyl)amines is described and their effects on prolonging effective refractory period in isolated cardiac tissue listed. Most compounds prolonged the cardiac action potential without significantly altering the maximum rate of depolarization and may be defined as selective class III antiarrhythmic agents. It was found that a particularly advantageous structural feature was to have a methanesulfonamido moiety on both of the aryl rings. Thus, compound 16 [1-(4-methanesulfonamidophenoxy)-2-[N-(4-methanesulfonamidophenethyl)- N-methylamine]ethane] was selected for further investigations. The compound is highly potent and selective class III agent which acts by blockade of cardiac potassium channels.