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CAS No.: | 120-20-7 |
---|---|
Name: | 3,4-Dimethoxyphenethylamine |
Article Data: | 110 |
Molecular Structure: | |
Formula: | C10H15NO2 |
Molecular Weight: | 181.235 |
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; |
EINECS: | 204-376-9 |
Density: | 1.041 g/cm3 |
Melting Point: | 12-15 ºC |
Boiling Point: | 324.1 ºC at 760 mmHg |
Flash Point: | 132.8 ºC |
Solubility: | Soluble in water |
Appearance: | colorless transparent liquid |
Hazard Symbols: | Xn |
Risk Codes: | 22-36/37/38 |
Safety: | 26-36-37/39 |
Transport Information: | UN 2735 |
PSA: | 44.48000 |
LogP: | 1.90530 |
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% |
(1S,4R)-2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-aza-bicyclo[2.2.1]hept-5-ene; hydrochloride
A
(1R,2S,6R,7S)-4-methyl-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione
B
6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
C
2-(3,4-dimethoxyphenyl)-ethylamine
Conditions | Yield |
---|---|
With N-methylmaleimide In water at 50℃; for 4h; | A 94% B 18% C 61% |
3,4-dimethoxynitrostyrene
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% |
2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-aza-bicyclo[2.2.1]hept-5-ene
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% |
1,2-dimethoxy-4-(2-nitroethyl)benzene
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 |
N-(2-hydroxybenzyl)-3,4-dimethoxyphenylethylamine
A
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 |
2-(3,4-dimethoxyphenyl)-ethylamine
Conditions | Yield |
---|---|
With indium; ammonium chloride In ethanol for 3h; Heating; | 76% |
N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide
2-(3,4-dimethoxyphenyl)-ethylamine
Conditions | Yield |
---|---|
With potassium carbonate In methanol; water for 2h; Heating; | 63% |
N,N'-(3,4-dimethoxy-β-phenylethyl)succindiamide
A
N-<2-(3,4-dimethoxyphenyl)ethyl>succinimide
B
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% |
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Reported in EPA TSCA Inventory.
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: XiXn
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.