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

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

Uses

Used in Pharmaceutical Industry:
4-Ethoxy-3-methoxyphenethylamine is used as a chemical intermediate for the synthesis of various pharmaceutical drugs. Its unique structural features allow it to be a versatile building block in the development of new medications with potential therapeutic benefits.
Used in Organic Chemistry Research:
In the field of organic chemistry, 4-ethoxy-3-methoxyphenethylamine is utilized as a research compound to explore its reactivity and potential use in the synthesis of novel organic compounds. Its unique substitution pattern on the phenyl ring makes it an interesting subject for studying reaction mechanisms and developing new synthetic methodologies.
Used in Psychopharmacology:
Due to its psychoactive properties, 4-ethoxy-3-methoxyphenethylamine may have potential applications in the development of new psychoactive substances. Researchers can use 4-ETHOXY-3-METHOXYPHENETHYLAMINE to investigate its effects on the central nervous system and explore its potential use in the treatment of various neurological and psychiatric disorders.
Used in Drug Development:
As a precursor in the production of pharmaceutical drugs, 4-ethoxy-3-methoxyphenethylamine plays a crucial role in drug development. Its unique structural features can be exploited to design and synthesize new drugs with improved pharmacological properties, such as increased potency, selectivity, and reduced side effects.

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

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

Downstream Products

• 1139890-75-7 2-(4-Ethoxy-3-methoxy-phenyl)-N-{2-[2-methyl-6-(2,4,6-trimethyl-phenylamino)-pyrimidin-4-ylamino]ethyl}-acetamide 
• 22231-68-1 benzo[1,3]dioxol-5-yl-acetic acid-(4-ethoxy-3-methoxy-phenethylamide) 
• 63905-74-8 7-ethoxy-6-methoxy-1,2,3,4-tetrahydro-isoquinoline; hydrochloride 
• 34162-18-0 2-chloro-N-(4-ethoxy-3-methoxyphenethyl)acetamide 

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