-
Name
3,4-Dimethoxyphenethylamine
- EINECS 204-376-9
- CAS No. 120-20-7
- Article Data110
- CAS DataBase
- Density 1.041 g/cm3
- Solubility Soluble in water
- Melting Point 12-15 ºC
- Formula C10H15NO2
- Boiling Point 324.1 ºC at 760 mmHg
- Molecular Weight 181.235
- Flash Point 132.8 ºC
- Transport Information UN 2735
- Appearance colorless transparent liquid
- Safety 26-36-37/39
- Risk Codes 22-36/37/38
-
Molecular Structure
-
Hazard Symbols
Xn
- Synonyms Phenethylamine,3,4-dimethoxy- (6CI,8CI);2-(3,4-Dimethoxyphenyl)ethanamine;2-(3,4-Dimethoxyphenyl)ethylamine;3,4-Di-O-methyldopamine;3,4-Dimethoxy-b-phenylethylamine;3,4-Dimethoxybenzeneethanamine;
- PSA 44.48000
- LogP 1.90530
Synthetic route
| Conditions | Yield |
|---|---|
| With hydrogen; palladium on activated charcoal In acetic acid for 4h; | 100% |
| Stage #1: 3,4-dimethoxyphenylacetonitrile With diborane In tetrahydrofuran at 55℃; for 16h; Inert atmosphere; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0 - 20℃; Stage #3: With sodium hydroxide In tetrahydrofuran; water | 99% |
| With hydrogen; nickel In ethanol at 40℃; electrocatalytic hydrogenation; | 98% |
| Conditions | Yield |
|---|---|
| With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran at 0 - 20℃; | 100% |
| With 5%-palladium/activated carbon; ammonium formate In methanol at 60 - 65℃; Temperature; Reagent/catalyst; Inert atmosphere; | 91.2% |
| With potassium borohydride; boron trifluoride diethyl etherate In tetrahydrofuran for 3h; Reflux; Green chemistry; | 87.5% |
-
-
110098-01-6
(1S,4R)-2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-aza-bicyclo[2.2.1]hept-5-ene; hydrochloride
-
A
-
3526-89-4, 6623-18-3, 56420-87-2
(1R,2S,6R,7S)-4-methyl-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione
-
B
-
1745-07-9
6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
-
C
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With N-methylmaleimide In water at 50℃; for 4h; | A 94% B 18% C 61% |
-
-
4230-93-7, 22568-47-4
3,4-dimethoxynitrostyrene
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 70℃; for 12h; Inert atmosphere; | 89% |
| With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux; | 84% |
| With lithium aluminium tetrahydride In tetrahydrofuran Reflux; | 76% |
-
-
126424-25-7, 150737-45-4
2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-aza-bicyclo[2.2.1]hept-5-ene
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| copper(II) sulfate In ethanol at 70℃; for 2h; | 82% |
| copper(II) sulfate In ethanol at 70℃; for 2h; other substrates, other catalysts; | 82% |
-
-
70360-83-7
1,2-dimethoxy-4-(2-nitroethyl)benzene
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 4h; Inert atmosphere; Green chemistry; chemoselective reaction; | 82% |
| With sodium tetrahydroborate; iron; water at 20℃; for 16h; | 82% |
| With hydrogenchloride; zinc |
-
-
171516-51-1
N-(2-hydroxybenzyl)-3,4-dimethoxyphenylethylamine
-
A
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| at 200℃; under 10 Torr; for 0.0833333h; Product distribution; pyrolysis without solvent, isolated as sulfate; | A 80% B n/a |
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With indium; ammonium chloride In ethanol for 3h; Heating; | 76% |
-
-
13230-71-2
N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With potassium carbonate In methanol; water for 2h; Heating; | 63% |
-
-
102897-57-4
N,N'-(3,4-dimethoxy-β-phenylethyl)succindiamide
-
A
-
39662-45-8
N-<2-(3,4-dimethoxyphenyl)ethyl>succinimide
-
B
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| Stage #1: N,N'-(3,4-dimethoxy-β-phenylethyl)succindiamide With sodium tetrahydroborate In methanol at 20℃; for 1h; Stage #2: With hydrogenchloride In water for 2h; Reflux; | A 30% B 50% |
-
-
771-51-7
indole-3-acetonitrile
-
-
93-17-4
3,4-dimethoxyphenylacetonitrile
-
A
-
53629-44-0
1-(3,4-dimethoxy-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline
-
B
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
C
-
168209-33-4
1-(3-methyl-1H-indole)-1,2,3,4-tetrahydro-β-carboline
| Conditions | Yield |
|---|---|
| With hydrogen; palladium In acetic acid for 72h; | A 37% B 14% C 28% D 16% |
-
-
93-17-4
3,4-dimethoxyphenylacetonitrile
-
A
-
24997-88-4
N-<2-(3,4-dimethoxyphenyl)ethyl>-2-(3,4-dimethoxyphenyl)ethylamine
-
B
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With hydrogen; palladium on activated charcoal In acetic acid for 48h; | A 35% B 35% C 10% |
-
-
126424-25-7, 150737-45-4
2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-aza-bicyclo[2.2.1]hept-5-ene
-
A
-
1745-07-9
6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
-
B
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With N-methylmaleimide | A 20% B n/a |
-
-
93-17-4
3,4-dimethoxyphenylacetonitrile
-
A
-
24997-88-4
N-<2-(3,4-dimethoxyphenyl)ethyl>-2-(3,4-dimethoxyphenyl)ethylamine
-
B
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With ethanol; nickel at 90℃; under 58840.6 Torr; Hydrogenation; |
-
-
54291-90-6
5-bromo-3,4-dimethoxy-1-(2-nitrovinyl)benzene
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With tetrahydrofuran; lithium aluminium tetrahydride |
-
-
57542-90-2
(dimethoxy-3,4 phenyl)-2 methoxy-2 nitro-1 ethane
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With sulfuric acid; palladium; acetic acid Hydrogenation; |
-
-
55446-63-4
4-(1,2-dibromo-2-nitro-ethyl)-1,2-dimethoxy-benzene
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With methanol; palladium Hydrogenation; |
-
-
14773-41-2
3-(3,4-dimethoxyphenyl)propionic acid amide
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With sodium hypochlorite at 70 - 75℃; | |
| With alkaline potassium hypochlorite und Eintragen des Reaktionprodukts in siedende Kalilauge; | |
| With potassium hypobromite auf dem Wasserbade; |
-
-
35167-81-8
3,4-dimethoxyphenethyl isocyanate
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With hydrogenchloride |
-
-
21997-97-7
3-(3,4-dimethoxy-phenyl)-propionyl azide
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With methanol und Erwaermen des Reaktionsprodukts mit wss.-aethanol.Kalilauge; | |
| With benzyl alcohol; benzene und Erwaermen des Reaktionsprodukts mit wss.Schwefelsaeure; | |
| With benzyl alcohol; benzene und Erwaermen des Reaktionsprodukts mit wss.Salzsaeure; | |
| With benzyl alcohol; benzene und Erwaermen des Reaktionsprodukts mit wss.Salzsaeure und Essigsaeure; | |
| Multi-step reaction with 2 steps 1: benzene 2: aqueous hydrochloric acid View Scheme |
-
-
77733-60-9
2-(3,4-dimethoxyphenyl)acetaldehyde oxime
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With ethanol; sodium | |
| Multi-step reaction with 2 steps 1: acetic acid anhydride 2: palladium; sulfuric acid; acetic acid / Hydrogenation View Scheme |
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With sulfuric acid; palladium; acetic acid Hydrogenation; |
-
-
13782-40-6
acetoxy-(3,4-dimethoxy-phenyl)-acetonitrile
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
| Conditions | Yield |
|---|---|
| With sulfuric acid; palladium; acetic acid Hydrogenation; |
-
-
104970-08-3
DL-1-(2,4-Dichlor-phenoxy)-3-<2-(3,4-dimethoxyphenyl)-ethylamino>propan-2-ol
-
A
-
94-75-7
2,4-Dichlorophenoxyacetic acid
-
B
-
23106-02-7
1-Amino-3-(2,4-dichloro-phenoxy)-propan-2-ol
-
C
-
34646-53-2
3-(2,4-dichloro-phenoxy)-propane-1,2-diol
-
D
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
E
-
121185-84-0
4-{2-[3-(2,4-Dichloro-phenoxy)-2-hydroxy-propylamino]-ethyl}-2-methoxy-phenol
-
F
-
120-83-2
2,4-dichlorophenol
| Conditions | Yield |
|---|---|
| biotransformation; |
-
A
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
124189-22-6, 124189-23-7
cis-octahydro-1H-2-benzopyran-1-one
| Conditions | Yield |
|---|---|
| With sulfuric acid for 2h; Heating; Yield given. Yields of byproduct given; |
-
A
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
124189-22-6, 124189-23-7
trans-octahydro-1H-2-benzopyran-1-one
| Conditions | Yield |
|---|---|
| With sulfuric acid for 2h; Heating; Yield given. Yields of byproduct given; |
-
A
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
B
-
156571-20-9
(1R,5S,7S)-1,5,7-Trimethyl-2,4-dioxo-3-oxa-bicyclo[3.3.1]nonane-7-carboxylic acid methyl ester
| Conditions | Yield |
|---|---|
| With water In acetonitrile at 37℃; Rate constant; buffer (pH 5.0-6.3); |
-
A
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
B
-
108694-84-4
(1R,5S,7R)-1,5,7-Trimethyl-2,4-dioxo-3-oxa-bicyclo[3.3.1]nonane-7-carboxylic acid methyl ester
| Conditions | Yield |
|---|---|
| With water In dimethyl sulfoxide at 22℃; Rate constant; buffer (pH 2.0-8.0); also in temp. 37 deg C (pH 5.0-6.3); |
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
108-30-5
succinic acid anhydride
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
39662-45-8
N-<2-(3,4-dimethoxyphenyl)ethyl>succinimide
| Conditions | Yield |
|---|---|
| With acetic acid for 24h; Reflux; | 100% |
| Stage #1: succinic acid anhydride; 2-(3,4-dimethoxyphenyl)-ethylamine In ethyl acetate at 20℃; for 0.5h; Stage #2: With acetyl chloride In toluene for 1h; Reflux; | 84% |
| With benzene und Erhitzen des Reaktionsprodukts mit Acetanhydrid unter Zusatz von wenig Pyridin; |
-
-
85-44-9
phthalic anhydride
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
26477-09-8
N-2-(3,4-dimethoxyphenyl)ethylphthalimide
| Conditions | Yield |
|---|---|
| Heating; | 100% |
| In methanol at 170 - 180℃; | 90% |
| at 100 - 150℃; Green chemistry; | 90% |
-
-
64-18-6
formic acid
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
14301-36-1
N-[2-(3,4-dimethoxyphenyl)ethyl]formamide
| Conditions | Yield |
|---|---|
| With acetic anhydride 1.) 60 deg C, 30 min, 2.) 20 deg C, overnight; | 100% |
| With 4-methyl-morpholine; dmap; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In dichloromethane at 35℃; for 0.05h; microwave irradiation; | 98% |
| In dichloromethane at 80℃; for 8h; | 95% |
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
79-04-9
chloroacetyl chloride
-
-
14301-31-6
2-chloro-N-(2-(3,4-dimethoxyphenyl)ethyl)acetamide
| Conditions | Yield |
|---|---|
| In dichloromethane | 100% |
| With N,N-dimethyl-aniline In dichloromethane at 0℃; for 1h; | 98% |
| With N,N-dimethyl-aniline In dichloromethane at 0℃; for 2h; | 98% |
| Conditions | Yield |
|---|---|
| With pyridine In acetonitrile at 20℃; for 3h; | 100% |
| With triethylamine In chloroform for 2h; Ambient temperature; | 73% |
| neat (no solvent); |
-
-
611-10-9
2-ethoxycarbonyl-1-cyclopentanone
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
130655-36-6
2-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-cyclopent-1-enecarboxylic acid ethyl ester
| Conditions | Yield |
|---|---|
| In ethanol at 100℃; for 1.33333h; | 100% |
| In ethanol at 100℃; for 2h; | |
| In chloroform at 70℃; Molecular sieve; |
-
-
774-05-0
ethyl cycloheptanone-2-carboxylate
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
130655-37-7
2-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-cyclohept-1-enecarboxylic acid ethyl ester
| Conditions | Yield |
|---|---|
| In ethanol at 100℃; | 100% |
| In ethanol at 100℃; for 2h; |
-
-
107-31-3
Methyl formate
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
14301-36-1
N-[2-(3,4-dimethoxyphenyl)ethyl]formamide
| Conditions | Yield |
|---|---|
| In methanol for 12h; Ambient temperature; | 100% |
| for 6h; Reflux; |
-
-
66757-48-0
methyl 4-formylhexanoate
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
78867-67-1
4-{[(E)-2-(3,4-Dimethoxy-phenyl)-ethylimino]-methyl}-hexanoic acid methyl ester
| Conditions | Yield |
|---|---|
| at 50 - 60℃; | 100% |
-
-
123001-21-8
(+)-(4S,5R)-4-(2-Benzyloxyethyl)-5-ethyl-3,4,5,6-tetrahydro-2-pyrone
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
122937-64-8
(+)-(3S,4R)-3-(2-Benzyloxyethyl)-N-(3,4-dimethoxyphenethyl)-4-hydroxymethylhexacarboxamide
| Conditions | Yield |
|---|---|
| at 155 - 165℃; for 6h; | 100% |
| at 135℃; Yield given; |
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
92884-66-7
N,N-Dimethyl-N'-(pyrrolidon-2-yl-1-acetyl)formamidine
-
A
-
7491-74-9
2-oxo-1-pyrrolidine acetamide
-
B
-
61945-49-1
N,N-dimethyl-N'-homoveratrylformamidine
| Conditions | Yield |
|---|---|
| In benzene for 4h; Ambient temperature; | A 100% B n/a |
| In benzene for 4h; Ambient temperature; |
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
75-36-5
acetyl chloride
-
-
6275-29-2
N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide
| Conditions | Yield |
|---|---|
| With triethylamine In dichloromethane | 100% |
| With triethylamine In dichloromethane at 0 - 26℃; Temperature; | 100% |
| With triethylamine In dichloromethane at 21℃; for 3h; | 97.7% |
-
-
120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine
-
-
109-94-4
formic acid ethyl ester
-
-
14301-36-1
N-[2-(3,4-dimethoxyphenyl)ethyl]formamide
| Conditions | Yield |
|---|---|
| at 70℃; for 20h; | 100% |
| at 70℃; | 100% |
| Reflux; | 99% |
3,4-Dimethoxyphenethylamine Consensus Reports
Reported in EPA TSCA Inventory.
3,4-Dimethoxyphenethylamine Specification
1. Introduction of 3,4-Dimethoxyphenethylamine
3,4-Dimethoxyphenethylamine is also called as 3,4-Di-O-methyldopamine; 3,4-Dimethoxy-beta-phenylethylamine; 3,4-Dimethoxybenzeneethanamine; 3,4-Dimethoxydopamine; 3,4-Dimethoxyphenylethylamine; 3,4-Dimethoxyphenylethylamine (base); 3,4-Dimethoxyphenylethylamine(base); Dimethoxydopamine; Dimethoxyphenylethylamine; Dimethylmescaline; Dopamine dimethyl ether; Homoveratrylamine; O,O-Dimethyldopamine; beta-(3,4-Dimethyoxyphenyl)ethylamine; 3,4-Dimethoxyphenethylamine; Benzeneethanamine, 3,4-dimethoxy-; Phenethylamine, 3,4-dimethoxy-. The IUPAC Name of 3,4-Dimethoxyphenethylamine is 2-(3,4-dimethoxyphenyl)ethanamine.
2. Properties of 3,4-Dimethoxyphenethylamine
Appearance: clear yellowish oil
Nominal Mass: 181 Da
Average Mass: 181.2316 Da
Monoisotopic Mass: 181.110279 Da
Index of Refraction: 1.517
Molar Refractivity: 52.69 cm3
Molar Volume: 173.9 cm3
Surface Tension: 36 dyne/cm
Density: 1.041 g/cm3
Flash Point: 132.8 °C
Enthalpy of Vaporization: 56.61 kJ/mol
Boiling Point: 324.1 °C at 760 mmHg
Vapour Pressure: 0.000251 mmHg at 25°C
Water Solubility: soluble
3. Structure Descriptors of 3,4-Dimethoxyphenethylamine
SMILES
O(c1ccc(cc1OC)CCN)C
InChI
InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3 Y
Key: ANOUKFYBOAKOIR-UHFFFAOYSA-N Y
InChI=1/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3
Key: ANOUKFYBOAKOIR-UHFFFAOYAB
4. Toxicity of 3,4-Dimethoxyphenethylamine
| 1. | ipr-mus LD50:181 mg/kg | YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. 97 (1977),1117. |
| 2. | ivn-mus LD50:56 mg/kg | CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals.(Aberdeen Proving Ground, MD 21010) NX#04483. |
5. Safety Information of 3,4-Dimethoxyphenethylamine
Poison by intravenous and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: 
Xi
Xn
Risk Statements: 22-36/37/38
R22: Harmful if swallowed
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36: Wear suitable protective clothing
S37/39: Wear suitable gloves and eye/face protection
RIDADR: UN 2735
WGK Germany :3
RTECS: SH2300000
F: 10
Hazard Note: Irritant
HazardClass: 8
PackingGroup: III
6. Preparation of 3,4-Dimethoxyphenethylamine
3,4-Dimethoxyphenethylamine can be prepared from 3-dimethyl benzene acetonitrile oxygen radicals via catalytic hydrogenation .
7. Use of 3,4-Dimethoxyphenethylamine
3,4-Dimethoxyphenethylamine can be used as intermediates in organic synthesis.
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