103-39-9

Basic information

• Product Name: 2-[(1-methyl-2-phenoxyethyl)amino]ethanol
• Synonyms: 2-[(1-methyl-2-phenoxyethyl)amino]ethanol;N-(Phenoxyisopropyl)ethanolamine;Einecs 203-107-2;2-((1-Phenoxypropan-2-yl)aMino)ethanol;2-[(1-Phenoxypropan-2-yl)amino]ethan-1-ol
• CAS NO: 103-39-9
• Molecular Formula: C₁₁H₁₇NO₂
• Molecular Weight: 195.25818
• EINECS: 203-107-2
• Mol File: 103-39-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 333.5 °C at 760 mmHg
• Flash Point: 155.5 °C
• Appearance: colorless or light yellow liquid
• Density: 1.048 /cm³
• Vapor Pressure: 5.4E-05mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Methanol
• CAS DataBase Reference: 2-[(1-methyl-2-phenoxyethyl)amino]ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(1-methyl-2-phenoxyethyl)amino]ethanol(103-39-9)
• EPA Substance Registry System: 2-[(1-methyl-2-phenoxyethyl)amino]ethanol(103-39-9)

Safety Data

• Hazardous Substances Data: 103-39-9(Hazardous Substances Data)

Usage

Uses

2-[(1-Methyl-2-phenoxyethyl)amino]ethanol is an intermediate in synthesizing N-?(2-?Chloroethyl)?-?1-?phenoxy-2-?propanamine Hydrochloride (C349003), which is the Impurity B of the drug Phenoxybenzamine Hydrochloride (P227990) which is an irreversible α-antagonist used in the treatment of hypertension. It has a relatively slow onset and prolonged effect when compared to alternative α-blockers.

InChI:InChI=1/C11H17NO2/c1-10(12-7-8-13)9-14-11-5-3-2-4-6-11/h2-6,10,12-13H,7-9H2,1H3

Synthetic route

1-phenoxypropane-2-yl-4-methylbenzene sulfonate (69333-63-7) + ethanolamine (141-43-5) → N-(phenoxyisopropyl)ethanolamine (103-39-9)

Conditions	Yield
at 110 - 115℃; for 2h;	77%

3-phenoxy-2-propanone (621-87-4) + ethanolamine (141-43-5) → N-(phenoxyisopropyl)ethanolamine (103-39-9)

Conditions	Yield
With methanol; nickel Hydrogenation.unter Druck;

ethanolamine (141-43-5) + (+-)-2-chloro-1-phenoxy-propane → N-(phenoxyisopropyl)ethanolamine (103-39-9)

1-phenoxy-2-propanol (770-35-4) → N-(phenoxyisopropyl)ethanolamine (103-39-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 10 - 35 °C 2: 2 h / 110 - 115 °C View Scheme

4-bromomethyl-1,2-dimethoxybenzene (21852-32-4) + N-(phenoxyisopropyl)ethanolamine (103-39-9) → 2-[(β-phenoxy-isopropyl)-veratryl-amino]-ethanol

Conditions	Yield
With toluene

9H-fluoren-9-yl bromide (1940-57-4) + N-(phenoxyisopropyl)ethanolamine (103-39-9) → 2-[fluoren-9-yl-(β-phenoxy-isopropyl)-amino]-ethanol

N-(phenoxyisopropyl)ethanolamine (103-39-9) + 1-chloromethyl-2-methylbenzene (552-45-4) → (2-chloro-ethyl)-(2-methyl-benzyl)-(β-phenoxy-isopropyl)-amine; hydrochloride

Conditions	Yield
With ethanol; sodium hydrogencarbonate anschliessend mit SOCl2 in CHCl3;
With ethanol; sodium hydrogencarbonate anschliessend mit SOCl2 in CHCl3;

N-(phenoxyisopropyl)ethanolamine (103-39-9) + 3,4-Dichlorophenylmethyl chloride (102-47-6) → (2-chloro-ethyl)-(3,4-dichloro-benzyl)-(β-phenoxy-isopropyl)-amine; hydrochloride

Conditions	Yield
With ethanol; potassium carbonate Erhitzen des Reaktionsprodukts mit SOCl2 in CHCl3;
With ethanol; sodium hydrogencarbonate Erhitzen des Reaktionsprodukts mit SOCl2 in CHCl3;
With ethanol; sodium hydrogencarbonate Erhitzen des Reaktionsprodukts mit SOCl2 in CHCl3;
With ethanol; potassium carbonate Erhitzen des Reaktionsprodukts mit SOCl2 in CHCl3;

N-(phenoxyisopropyl)ethanolamine (103-39-9) + 2,4-Dichlorobenzyl chloride (94-99-5) → 2-[(2,4-dichloro-benzyl)-(β-phenoxy-isopropyl)-amino]-ethanol

Conditions	Yield
With ethanol; sodium hydrogencarbonate

N-(phenoxyisopropyl)ethanolamine (103-39-9) + benzyl chloride (100-44-7) → N-(phenoxyisopropyl)-N-benzyl ethanolamine (101-45-1)

Conditions	Yield
With ethanol; sodium hydrogencarbonate
With sodium hydrogencarbonate In ethanol at 25 - 80℃; for 20h;
With ethanol; sodium hydrogencarbonate

N-(phenoxyisopropyl)ethanolamine (103-39-9) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) → 2-[(4-chloro-benzyl)-(β-phenoxy-isopropyl)-amino]-ethanol (875243-78-0)

Conditions	Yield
With ethanol; potassium carbonate

N-(phenoxyisopropyl)ethanolamine (103-39-9) + p-methoxybenzyl chloride (824-94-2) → (2-chloro-ethyl)-(4-methoxy-benzyl)-(β-phenoxy-isopropyl)-amine

Conditions	Yield
nachfolgende Umsetzung mit SOCl2;

N-(phenoxyisopropyl)ethanolamine (103-39-9) → (2-chloro-ethyl)-(4-chloro-benzyl)-(β-phenoxy-isopropyl)-amine; hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3; ethanol 2: CHCl3; SOCl2 View Scheme

N-(phenoxyisopropyl)ethanolamine (103-39-9) → (2-chloro-ethyl)-(β-phenoxy-isopropyl)-veratryl-amine; hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene 2: CHCl3; HCl; SOCl2 View Scheme

Upstream product

• 621-87-4 3-phenoxy-2-propanone 
• 141-43-5 ethanolamine 
• 770-35-4 1-phenoxy-2-propanol 
• 69333-63-7 1-phenoxypropane-2-yl-4-methylbenzene sulfonate 

Downstream Products

• 101-45-1 N-(phenoxyisopropyl)-N-benzyl ethanolamine 
• 875243-78-0 2-[(4-chloro-benzyl)-(β-phenoxy-isopropyl)-amino]-ethanol 

Relevant articles and documents

A PROCESS FOR THE PREPARATION OF PHENOXYBENZAMINE

The present invention provides a process for the preparation of N-phenoxyisopropyl ethanolamine of Formula (II) and its conversion to Phenoxybenzamine of Formula (I) or pharmaceutically acceptable salts thereof.