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3,4-Dimethoxyphenethylamine
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Name

3,4-Dimethoxyphenethylamine

 EINECS 204-376-9
CAS No. 120-20-7 Density 1.041 g/cm3
PSA 44.48000 LogP 1.90530
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 Molecular Structure of 120-20-7 (3,4-Dimethoxyphenethylamine) Hazard Symbols HarmfulXn
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;

Article Data 110

3,4-Dimethoxyphenethylamine Synthetic route

93-17-4

3,4-dimethoxyphenylacetonitrile

120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
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%
4230-93-7

1,2-dimethoxy-4-(2-nitro-vinyl)-benzene

120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

B

C21H18O3

Conditions
ConditionsYield
at 200℃; under 10 Torr; for 0.0833333h; Product distribution; pyrolysis without solvent, isolated as sulfate;A 80%
B n/a

[2-(3,4-dimethoxy-phenyl)-ethyl]-carbamic acid 2,2,2-trichloro-ethyl ester

120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%

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: IrritantXiHarmfulXn
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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