36377-59-0

Basic information

• Product Name: 4-ETHOXY-3-METHOXYPHENETHYLAMINE
• Synonyms: RARECHEM AL BW 0365;4-ETHOXY-3-METHOXYPHENETHYLAMINE;AKOS 235-25;2-(4-Ethoxy-3-methoxyphenyl)ethanamine;4-ETHOXY-3-METHOXYPHENETHYLAMINE 99%
• CAS NO: 36377-59-0
• Molecular Formula: C₁₁H₁₇NO₂
• Molecular Weight: 195.26
• Mol File: 36377-59-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 113°C 1mm
• Flash Point: 144.1 °C
• Appearance: /
• Density: 1,04 g/cm3
• Vapor Pressure: 0.00154mmHg at 25°C
• Refractive Index: 1.513
• PKA: 9.75±0.10(Predicted)
• CAS DataBase Reference: 4-ETHOXY-3-METHOXYPHENETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ETHOXY-3-METHOXYPHENETHYLAMINE(36377-59-0)
• EPA Substance Registry System: 4-ETHOXY-3-METHOXYPHENETHYLAMINE(36377-59-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT, IRRITANT-HARMFUL
• Hazardous Substances Data: 36377-59-0(Hazardous Substances Data)

Usage

General Description

4-Ethoxy-3-methoxyphenethylamine is a chemical compound that belongs to the class of phenethylamines. It is a derivative of 3-Methoxy-4-ethoxyphenethylamine, containing an additional ethoxy group on the para position of the phenyl ring. 4-ETHOXY-3-METHOXYPHENETHYLAMINE is not commonly found in nature and is primarily synthesized for research and experimental purposes. It can be used as a precursor in the production of various pharmaceutical drugs and may also have potential applications in the field of organic chemistry. Due to its psychoactive properties, it may also have potential use in the development of new psychoactive substances. However,

InChI:InChI=1/C11H17NO2/c1-3-14-10-5-4-9(6-7-12)8-11(10)13-2/h4-5,8H,3,6-7,12H2,1-2H3

Synthetic route

4-ethoxy-3-methoxy-β-nitro-styrene (54110-88-2) → 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0)

Conditions	Yield
at 65℃; bei der elektrolytischen Reduktion;
With hydrogenchloride; ethanol at 65℃; Electrolysis.bei der elektrolytischen Reduktion an Bleikathoden;
With lithium aluminium tetrahydride; diethyl ether; benzene

4-ethoxy-3-methoxybenzylcyanide (103796-52-7) → 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0)

Conditions	Yield
With ammonia; nickel at 120 - 140℃; under 91938.4 Torr; Hydrogenation;
With sodium hydroxide; nickel Hydrogenation;

3-(4-ethoxy-3-methoxy-phenyl)-propionic acid amide (858783-47-8) → 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0)

Conditions	Yield
With potassium hypobromite
With sodium hypochlorite

3-(4-ethoxy-3-methoxy-phenyl)-propionic acid hydrazide (121670-34-6) → 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0)

Conditions	Yield
With hydrogenchloride; diethyl ether; sodium nitrite Erwaermen des Reaktionsprodukts mit Aethanol und anschliessend mit wss.NaOH;

4-ethoxy-3-methoxy-β-nitro-styrene (54110-88-2) + acetic acid (64-19-7) + hydrogen + platinum → 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0)

Conditions	Yield
nachfolgend Reduktion mit Natriumamalgam in Essigsaeure;

ethanol (64-17-5) + 4-ethoxy-3-methoxy-β-nitro-styrene (54110-88-2) + acetic acid (64-19-7) + zinc dust → 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0)

Conditions	Yield
nachfolgend Reduktion mit Natriumamalgam;

3-methoxy-4-ethoxy-DL-mandelonitrile → 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) + 1-(4-ethoxy-3-methoxy-phenyl)-2-amino-ethanol

Conditions	Yield
With palladium; acetic acid Hydrogenation;

1-ethoxy-4-chloromethyl-2-methoxy-benzene (53979-18-3) → 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene 2: Raney nickel; ethanolic NH3 / 120 - 140 °C / 91938.4 Torr / Hydrogenation View Scheme

3-(4-ethoxy-3-methoxyphenyl)-propionic acid (30044-91-8) → 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride; chloroform / Eintragen des Reaktionsgemisches in ein Gemisch von wss. Natronlauge und wss. Ammoniak 2: aqueous sodium hypochlorite View Scheme

C11H15NO4 → 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0)

Conditions	Yield
With hydrogenchloride; zinc In ethanol; water for 3h;

4-ethoxy-3-methoxybenzaldehyde (120-25-2) → 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: methylamine / methanol / 3.5 h / 50 °C 2: sodium tetrahydroborate; methanol / 2 h / Reflux 3: zinc; hydrogenchloride / ethanol; water / 3 h View Scheme

6-bromohomoveratric acid (4697-62-5) + 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) → 2-(2-bromo-4,5-dimethoxyphenyl)-N-(4-ethoxy-3-methoxyphenethyl)acetamide

Conditions	Yield
Stage #1: 6-bromohomoveratric acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1h; Stage #2: 2-(4-ethoxy-3-methoxyphenyl)ethylamine In tetrahydrofuran at 0 - 20℃;	75%

4,5-methylenedioxy-2-nitrobenzoyl chloride (50425-29-1) + 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) → 6-Nitro-benzo[1,3]dioxole-5-carboxylic acid [2-(4-ethoxy-3-methoxy-phenyl)-ethyl]-amide (125232-03-3)

Conditions	Yield
In benzene Ambient temperature;	25%

2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) + 2-nitrobenzyl chloride (610-14-0) → N-[2-(4-Ethoxy-3-methoxy-phenyl)-ethyl]-2-nitro-benzamide (125232-02-2)

Conditions	Yield
In benzene Ambient temperature;	23%

2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) + 4-Ethoxy-5-methoxy-2-nitro-benzoyl chloride → 4-Ethoxy-N-[2-(4-ethoxy-3-methoxy-phenyl)-ethyl]-5-methoxy-2-nitro-benzamide (125232-05-5)

Conditions	Yield
In benzene Ambient temperature;	21%

2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) + 4,5-dimethoxy-2-nitrobenzoyl chloride (29568-78-3) → N-[2-(4-Ethoxy-3-methoxy-phenyl)-ethyl]-4,5-dimethoxy-2-nitro-benzamide (125232-04-4)

Conditions	Yield
In benzene Ambient temperature;	10%

formaldehyd (50-00-0) + 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) → 7-ethoxy-6-methoxy-1,2,3,4-tetrahydro-isoquinoline; hydrochloride (63905-74-8)

Conditions	Yield
With water und Erwaermen des Reaktionsprodukts mit wss. Salzsaeure;

nitrourea (556-89-8) + 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) → (4-ethoxy-3-methoxy-phenethyl)-urea

Conditions	Yield
With ethanol

homopiperonylic acid + 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) → benzo[1,3]dioxol-5-yl-acetic acid-(4-ethoxy-3-methoxy-phenethylamide) (22231-68-1)

Conditions	Yield
at 200℃;

2-ethoxylbenzaldehyde (613-69-4) + 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) → (2-ethoxy-benzyl)-(4-ethoxy-3-methoxy-phenethyl)-amine

Conditions	Yield
With acetic acid; platinum Hydrogenation;

3-ethoxybenzaldehyde (22924-15-8) + 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) → (3-ethoxy-benzyl)-(4-ethoxy-3-methoxy-phenethyl)-amine

Conditions	Yield
With acetic acid; platinum Hydrogenation;

3,4-diethoxybenzaldehyde (2029-94-9) + 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) → (4-ethoxy-3-methoxy-phenethyl)-(3,4-diethoxy-benzyliden)-amine

Conditions	Yield
unter vermindertem Druck;

2,2'-(oxydibenzene-4 1-diyl)diacetic acid (5633-43-2) + 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) → 7,7'-diethoxy-6,6'-dimethoxy-2,2,2',2'-tetramethyl-1,2,3,4,1',2',3',4'-octahydro-1,1'-(4,4'-oxy-di-benzyl)-bis-isoquinolinium; diiodide

Conditions	Yield
With tetralin Erwaermen des Reaktionsprodukts in Chloroform mit Phosphorylchlorid,Hydrieren des erhaltenen Reaktionsprodukts an Raney-Nickel in Methanol unter Zusatz von Natriumacetat bei 105grad/50 at,Behandeln des Reaktionsprodukts mit; Dimethylsulfat und wss.Natronlauge in Tetrahydrofuran und anschliessenden Ueberfuehren in das Dijodid mit Hilfe von Natriumjodid.;
With tetralin Erwaermen des Reaktionsprodukts in Chloroform mit Phosphorylchlorid,Hydrieren des erhaltenen Reaktionsprodukts an Platin in Wasser,Behandeln des Reaktionsprodukts mit Dimethylsulfat und wss.Natronlauge in Tetrahydrofuran; und anschliessenden Ueberfuehren in das Dijodid mit Hilfe von Natriumjodid.;

2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) + 3,4-diethoxybenzoyl chloride (105905-60-0) → 3,4-diethoxy-benzoic acid-(4-ethoxy-3-methoxy-phenethylamide) (855269-82-8)

Conditions	Yield
With pyridine

2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) + 2-diazo-1-(3-methoxy-2-nitro-phenyl)-ethanone (24115-83-1) → (3-methoxy-2-nitro-phenyl)-acetic acid-(4-ethoxy-3-methoxy-phenethylamide) (110332-38-2)

Conditions	Yield
With silver(l) oxide; benzene

2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) + (5-ethoxy-4-methoxy-2-nitro-phenyl)-acetic acid (858843-13-7) → (5-ethoxy-4-methoxy-2-nitro-phenyl)-acetic acid-(4-ethoxy-3-methoxy-phenethylamide)

2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) + 3-(4-ethoxy-3-methoxy-phenyl)-propionyl azide → 3-(4-ethoxy-3-methoxy-phenyl)-propionic acid-(4-ethoxy-3-methoxy-phenethylamide)

2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) + chloroformic acid ethyl ester (541-41-3) → 7-ethoxy-6-methoxy-1,2,3,4-tetrahydroisoquinolin-1-one (16562-11-1)

Conditions	Yield
With alkaline solution beim Erhitzen mit Phosphoroxychlorid und wenig Phosphorpentoxyd in Xylol auf 140gradC;

2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) + 4-ethoxybenzaldehyde (10031-82-0) → (4-ethoxy-benzyliden)-(4-ethoxy-3-methoxy-phenethyl)-amine

Conditions	Yield
unter vermindertem Druck;

2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) + benzaldehyde (100-52-7) → (4-ethoxy-3-methoxy-phenethyl)-benzyliden-amine

Conditions	Yield
unter vermindertem Druck;

2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) + benzaldehyde (100-52-7) + methyl iodide (74-88-4) → (4-ethoxy-3-methoxy-phenethyl)-methyl-amine (861008-07-3)

Conditions	Yield
und Erwaermen des Reaktionsprodukts mit wss.Aethanol;

formic acid (64-18-6) + 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) → N-(4-ethoxy-3-methoxy-phenethyl)-formamide (857789-78-7)

Conditions	Yield
at 160℃; for 5h;

4-Methoxyphenylacetic acid (104-01-8) + 2-(4-ethoxy-3-methoxyphenyl)ethylamine (36377-59-0) → N-<3-Methoxy-4-aethoxy-phenaethyl>-4-methoxy-phenylacetamid (16543-74-1)

Conditions	Yield
In xylene

Upstream product

• 54110-88-2 4-ethoxy-3-methoxy-β-nitro-styrene 
• 103796-52-7 4-ethoxy-3-methoxybenzylcyanide 
• 858783-47-8 3-(4-ethoxy-3-methoxy-phenyl)-propionic acid amide 
• 121670-34-6 3-(4-ethoxy-3-methoxy-phenyl)-propionic acid hydrazide 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 53979-18-3 1-ethoxy-4-chloromethyl-2-methoxy-benzene 
• 30044-91-8 3-(4-ethoxy-3-methoxyphenyl)-propionic acid 
• 120-25-2 4-ethoxy-3-methoxybenzaldehyde 
• 121-33-5 vanillin 

Downstream Products

• 63905-74-8 7-ethoxy-6-methoxy-1,2,3,4-tetrahydro-isoquinoline; hydrochloride 
• 22231-68-1 benzo[1,3]dioxol-5-yl-acetic acid-(4-ethoxy-3-methoxy-phenethylamide) 
• 855269-82-8 3,4-diethoxy-benzoic acid-(4-ethoxy-3-methoxy-phenethylamide) 
• 110332-38-2 (3-methoxy-2-nitro-phenyl)-acetic acid-(4-ethoxy-3-methoxy-phenethylamide) 
• 861008-07-3 (4-ethoxy-3-methoxy-phenethyl)-methyl-amine 
• 125232-03-3 6-Nitro-benzo[1,3]dioxole-5-carboxylic acid [2-(4-ethoxy-3-methoxy-phenyl)-ethyl]-amide 
• 125232-04-4 N-[2-(4-Ethoxy-3-methoxy-phenyl)-ethyl]-4,5-dimethoxy-2-nitro-benzamide 
• 125232-02-2 N-[2-(4-Ethoxy-3-methoxy-phenyl)-ethyl]-2-nitro-benzamide 
• 16543-74-1 N-<3-Methoxy-4-aethoxy-phenaethyl>-4-methoxy-phenylacetamid 
• 51598-65-3 (4,5-dimethoxy-2-nitro-phenyl)-acetic acid-(4-ethoxy-3-methoxy-phenethylamide) 
• 125232-14-6 2-Amino-4-ethoxy-N-[2-(4-ethoxy-3-methoxy-phenyl)-ethyl]-5-methoxy-benzamide 
• 125232-22-6 7-Ethoxy-3-[2-(4-ethoxy-3-methoxy-phenyl)-ethyl]-6-methoxy-3H-quinazolin-4-one 

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