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120-20-7

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120-20-7 Usage

Chemical Properties

3,4-Dimethoxyphenethylamine is clear yellowish oil

Uses

Different sources of media describe the Uses of 120-20-7 differently. You can refer to the following data:
1. 3,4-Dimethoxyphenethylamine is a methylated metabolite of Dopamine (D533780); a potent inhibitor of brain mitochondrial respiration used in Parkinson’s disease studies.
2. A methylated metabolite of Dopamine (D533780); a potent inhibitor of brain mitochondrial respiration used in Parkinson’s disease studies.
3. Precursor for the synthesis of isoquinolines.

Definition

ChEBI: An aromatic ether that is the derivative of 2-phenylethylamine with methoxy substituents at the 3- and 4-positions. It is an alkaloid isolated from the Cactaceae family.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by intravenous and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Purify the amine by fractionation through an efficient column in an inert atmosphere as it is a relatively strong base. [Horner & Sturm Justus Liebigs Ann Chem 608 12819 1957, Jung et al. J Am Chem Soc 75 4664 1953.] The hydrochloride has m 152o, 154o, 156o (from EtOH, Me2CO or EtOH/Et2O), the picrate has m 165-167o(dec), and the 4-nitrobenzoyl derivative has m 147o [Buck J Am Chem Soc 55 2593 1933]. [Beilstein 13 H 800, 13 IV 2604.]

Check Digit Verification of cas no

The CAS Registry Mumber 120-20-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 0 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 120-20:
(5*1)+(4*2)+(3*0)+(2*2)+(1*0)=17
17 % 10 = 7
So 120-20-7 is a valid CAS Registry Number.
InChI: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

120-20-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,4-dimethoxyphenylethylamine

1.2 Other means of identification

Product number -
Other names 3,4-Dimethoxyphenethylamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:120-20-7 SDS

120-20-7Synthetic route

3,4-dimethoxyphenylacetonitrile
93-17-4

3,4-dimethoxyphenylacetonitrile

2-(3,4-dimethoxyphenyl)-ethylamine
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%
1,2-dimethoxy-4-(2-nitro-vinyl)-benzene
4230-93-7

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

2-(3,4-dimethoxyphenyl)-ethylamine
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%
(1S,4R)-2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-aza-bicyclo[2.2.1]hept-5-ene; hydrochloride
110098-01-6

(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
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

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
1745-07-9

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

C

2-(3,4-dimethoxyphenyl)-ethylamine
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%
3,4-dimethoxynitrostyrene
4230-93-7, 22568-47-4

3,4-dimethoxynitrostyrene

2-(3,4-dimethoxyphenyl)-ethylamine
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%
2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-aza-bicyclo[2.2.1]hept-5-ene
126424-25-7, 150737-45-4

2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-aza-bicyclo[2.2.1]hept-5-ene

2-(3,4-dimethoxyphenyl)-ethylamine
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%
1,2-dimethoxy-4-(2-nitroethyl)benzene
70360-83-7

1,2-dimethoxy-4-(2-nitroethyl)benzene

2-(3,4-dimethoxyphenyl)-ethylamine
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
N-(2-hydroxybenzyl)-3,4-dimethoxyphenylethylamine
171516-51-1

N-(2-hydroxybenzyl)-3,4-dimethoxyphenylethylamine

A

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

B

C21H18O3

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

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

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
With indium; ammonium chloride In ethanol for 3h; Heating;76%
N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide
13230-71-2

N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
With potassium carbonate In methanol; water for 2h; Heating;63%
N,N'-(3,4-dimethoxy-β-phenylethyl)succindiamide
102897-57-4

N,N'-(3,4-dimethoxy-β-phenylethyl)succindiamide

A

N-<2-(3,4-dimethoxyphenyl)ethyl>succinimide
39662-45-8

N-<2-(3,4-dimethoxyphenyl)ethyl>succinimide

B

2-(3,4-dimethoxyphenyl)-ethylamine
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%
indole-3-acetonitrile
771-51-7

indole-3-acetonitrile

3,4-dimethoxyphenylacetonitrile
93-17-4

3,4-dimethoxyphenylacetonitrile

A

1-(3,4-dimethoxy-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline
53629-44-0

1-(3,4-dimethoxy-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline

B

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

C

1-(3-methyl-1H-indole)-1,2,3,4-tetrahydro-β-carboline
168209-33-4

1-(3-methyl-1H-indole)-1,2,3,4-tetrahydro-β-carboline

D

Tris-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine

Tris-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine

Conditions
ConditionsYield
With hydrogen; palladium In acetic acid for 72h;A 37%
B 14%
C 28%
D 16%
3,4-dimethoxyphenylacetonitrile
93-17-4

3,4-dimethoxyphenylacetonitrile

A

N-<2-(3,4-dimethoxyphenyl)ethyl>-2-(3,4-dimethoxyphenyl)ethylamine
24997-88-4

N-<2-(3,4-dimethoxyphenyl)ethyl>-2-(3,4-dimethoxyphenyl)ethylamine

B

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

C

Tris-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine

Tris-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In acetic acid for 48h;A 35%
B 35%
C 10%
2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-aza-bicyclo[2.2.1]hept-5-ene
126424-25-7, 150737-45-4

2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-aza-bicyclo[2.2.1]hept-5-ene

A

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
1745-07-9

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

B

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
With N-methylmaleimideA 20%
B n/a
3,4-dimethoxyphenylacetonitrile
93-17-4

3,4-dimethoxyphenylacetonitrile

A

N-<2-(3,4-dimethoxyphenyl)ethyl>-2-(3,4-dimethoxyphenyl)ethylamine
24997-88-4

N-<2-(3,4-dimethoxyphenyl)ethyl>-2-(3,4-dimethoxyphenyl)ethylamine

B

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
With ethanol; nickel at 90℃; under 58840.6 Torr; Hydrogenation;
5-bromo-3,4-dimethoxy-1-(2-nitrovinyl)benzene
54291-90-6

5-bromo-3,4-dimethoxy-1-(2-nitrovinyl)benzene

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
With tetrahydrofuran; lithium aluminium tetrahydride
(dimethoxy-3,4 phenyl)-2 methoxy-2 nitro-1 ethane
57542-90-2

(dimethoxy-3,4 phenyl)-2 methoxy-2 nitro-1 ethane

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
With sulfuric acid; palladium; acetic acid Hydrogenation;
4-(1,2-dibromo-2-nitro-ethyl)-1,2-dimethoxy-benzene
55446-63-4

4-(1,2-dibromo-2-nitro-ethyl)-1,2-dimethoxy-benzene

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
With methanol; palladium Hydrogenation;
3-(3,4-dimethoxyphenyl)propionic acid amide
14773-41-2

3-(3,4-dimethoxyphenyl)propionic acid amide

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
With sodium hypochlorite at 70 - 75℃;
With alkaline potassium hypochlorite und Eintragen des Reaktionprodukts in siedende Kalilauge;
With potassium hypobromite auf dem Wasserbade;
3,4-dimethoxyphenethyl isocyanate
35167-81-8

3,4-dimethoxyphenethyl isocyanate

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
With hydrogenchloride
3-(3,4-dimethoxy-phenyl)-propionyl azide
21997-97-7

3-(3,4-dimethoxy-phenyl)-propionyl azide

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
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
2-(3,4-dimethoxyphenyl)acetaldehyde oxime
77733-60-9

2-(3,4-dimethoxyphenyl)acetaldehyde oxime

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
With ethanol; sodium
Multi-step reaction with 2 steps
1: acetic acid anhydride
2: palladium; sulfuric acid; acetic acid / Hydrogenation
View Scheme
(3,4-dimethoxy-phenyl)-glyoxal-2-oxime

(3,4-dimethoxy-phenyl)-glyoxal-2-oxime

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
With sulfuric acid; palladium; acetic acid Hydrogenation;
acetoxy-(3,4-dimethoxy-phenyl)-acetonitrile
13782-40-6

acetoxy-(3,4-dimethoxy-phenyl)-acetonitrile

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Conditions
ConditionsYield
With sulfuric acid; palladium; acetic acid Hydrogenation;
DL-1-(2,4-Dichlor-phenoxy)-3-<2-(3,4-dimethoxyphenyl)-ethylamino>propan-2-ol
104970-08-3

DL-1-(2,4-Dichlor-phenoxy)-3-<2-(3,4-dimethoxyphenyl)-ethylamino>propan-2-ol

A

2,4-Dichlorophenoxyacetic acid
94-75-7

2,4-Dichlorophenoxyacetic acid

B

1-Amino-3-(2,4-dichloro-phenoxy)-propan-2-ol
23106-02-7

1-Amino-3-(2,4-dichloro-phenoxy)-propan-2-ol

C

3-(2,4-dichloro-phenoxy)-propane-1,2-diol
34646-53-2

3-(2,4-dichloro-phenoxy)-propane-1,2-diol

D

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

E

4-{2-[3-(2,4-Dichloro-phenoxy)-2-hydroxy-propylamino]-ethyl}-2-methoxy-phenol
121185-84-0

4-{2-[3-(2,4-Dichloro-phenoxy)-2-hydroxy-propylamino]-ethyl}-2-methoxy-phenol

F

2,4-dichlorophenol
120-83-2

2,4-dichlorophenol

Conditions
ConditionsYield
biotransformation;
[2-(3,4-Dimethoxy-phenyl)-ethyl]-(4aR,8aR)-octahydro-isochromen-(1Z)-ylidene-amine; hydrochloride

[2-(3,4-Dimethoxy-phenyl)-ethyl]-(4aR,8aR)-octahydro-isochromen-(1Z)-ylidene-amine; hydrochloride

A

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

cis-octahydro-1H-2-benzopyran-1-one
124189-22-6, 124189-23-7

cis-octahydro-1H-2-benzopyran-1-one

Conditions
ConditionsYield
With sulfuric acid for 2h; Heating; Yield given. Yields of byproduct given;
[2-(3,4-Dimethoxy-phenyl)-ethyl]-(4aS,8aR)-octahydro-isochromen-(1Z)-ylidene-amine; hydrochloride

[2-(3,4-Dimethoxy-phenyl)-ethyl]-(4aS,8aR)-octahydro-isochromen-(1Z)-ylidene-amine; hydrochloride

A

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

trans-octahydro-1H-2-benzopyran-1-one
124189-22-6, 124189-23-7

trans-octahydro-1H-2-benzopyran-1-one

Conditions
ConditionsYield
With sulfuric acid for 2h; Heating; Yield given. Yields of byproduct given;
(1R,3S,5R)-5-[2-(3,4-Dimethoxy-phenyl)-ethylcarbamoyl]-1,3,5-trimethyl-cyclohexane-1,3-dicarboxylic acid monomethyl ester

(1R,3S,5R)-5-[2-(3,4-Dimethoxy-phenyl)-ethylcarbamoyl]-1,3,5-trimethyl-cyclohexane-1,3-dicarboxylic acid monomethyl ester

A

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

B

(1R,5S,7S)-1,5,7-Trimethyl-2,4-dioxo-3-oxa-bicyclo[3.3.1]nonane-7-carboxylic acid methyl ester
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
ConditionsYield
With water In acetonitrile at 37℃; Rate constant; buffer (pH 5.0-6.3);
(1S,3S,5R)-5-[2-(3,4-Dimethoxy-phenyl)-ethylcarbamoyl]-1,3,5-trimethyl-cyclohexane-1,3-dicarboxylic acid monomethyl ester

(1S,3S,5R)-5-[2-(3,4-Dimethoxy-phenyl)-ethylcarbamoyl]-1,3,5-trimethyl-cyclohexane-1,3-dicarboxylic acid monomethyl ester

A

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

B

(1R,5S,7R)-1,5,7-Trimethyl-2,4-dioxo-3-oxa-bicyclo[3.3.1]nonane-7-carboxylic acid methyl ester
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
ConditionsYield
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);
3,4-dimethoxy<α-14C>phenethylamine

3,4-dimethoxy<α-14C>phenethylamine

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

succinic acid anhydride
108-30-5

succinic acid anhydride

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

N-<2-(3,4-dimethoxyphenyl)ethyl>succinimide
39662-45-8

N-<2-(3,4-dimethoxyphenyl)ethyl>succinimide

Conditions
ConditionsYield
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;
phthalic anhydride
85-44-9

phthalic anhydride

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

N-2-(3,4-dimethoxyphenyl)ethylphthalimide
26477-09-8

N-2-(3,4-dimethoxyphenyl)ethylphthalimide

Conditions
ConditionsYield
Heating;100%
In methanol at 170 - 180℃;90%
at 100 - 150℃; Green chemistry;90%
formic acid
64-18-6

formic acid

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

N-[2-(3,4-dimethoxyphenyl)ethyl]formamide
14301-36-1

N-[2-(3,4-dimethoxyphenyl)ethyl]formamide

Conditions
ConditionsYield
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%
2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-chloro-N-(2-(3,4-dimethoxyphenyl)ethyl)acetamide
14301-31-6

2-chloro-N-(2-(3,4-dimethoxyphenyl)ethyl)acetamide

Conditions
ConditionsYield
In dichloromethane100%
With N,N-dimethyl-aniline In dichloromethane at 0℃; for 1h;98%
With N,N-dimethyl-aniline In dichloromethane at 0℃; for 2h;98%
2-furancarbonyl chloride
527-69-5

2-furancarbonyl chloride

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

N-<2-(3,4-dimethoxyphenyl)ethyl>furan-2-carboxamide

N-<2-(3,4-dimethoxyphenyl)ethyl>furan-2-carboxamide

Conditions
ConditionsYield
With pyridine In acetonitrile at 20℃; for 3h;100%
With triethylamine In chloroform for 2h; Ambient temperature;73%
neat (no solvent);
2-ethoxycarbonyl-1-cyclopentanone
611-10-9

2-ethoxycarbonyl-1-cyclopentanone

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

2-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-cyclopent-1-enecarboxylic acid ethyl ester
130655-36-6

2-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-cyclopent-1-enecarboxylic acid ethyl ester

Conditions
ConditionsYield
In ethanol at 100℃; for 1.33333h;100%
In ethanol at 100℃; for 2h;
In chloroform at 70℃; Molecular sieve;
ethyl cycloheptanone-2-carboxylate
774-05-0

ethyl cycloheptanone-2-carboxylate

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

2-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-cyclohept-1-enecarboxylic acid ethyl ester
130655-37-7

2-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-cyclohept-1-enecarboxylic acid ethyl ester

Conditions
ConditionsYield
In ethanol at 100℃;100%
In ethanol at 100℃; for 2h;
Methyl formate
107-31-3

Methyl formate

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

N-[2-(3,4-dimethoxyphenyl)ethyl]formamide
14301-36-1

N-[2-(3,4-dimethoxyphenyl)ethyl]formamide

Conditions
ConditionsYield
In methanol for 12h; Ambient temperature;100%
for 6h; Reflux;
methyl 4-formylhexanoate
66757-48-0

methyl 4-formylhexanoate

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

4-{[(E)-2-(3,4-Dimethoxy-phenyl)-ethylimino]-methyl}-hexanoic acid methyl ester
78867-67-1

4-{[(E)-2-(3,4-Dimethoxy-phenyl)-ethylimino]-methyl}-hexanoic acid methyl ester

Conditions
ConditionsYield
at 50 - 60℃;100%
(+)-(4S,5R)-4-(2-Benzyloxyethyl)-5-ethyl-3,4,5,6-tetrahydro-2-pyrone
123001-21-8

(+)-(4S,5R)-4-(2-Benzyloxyethyl)-5-ethyl-3,4,5,6-tetrahydro-2-pyrone

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

(+)-(3S,4R)-3-(2-Benzyloxyethyl)-N-(3,4-dimethoxyphenethyl)-4-hydroxymethylhexacarboxamide
122937-64-8

(+)-(3S,4R)-3-(2-Benzyloxyethyl)-N-(3,4-dimethoxyphenethyl)-4-hydroxymethylhexacarboxamide

Conditions
ConditionsYield
at 155 - 165℃; for 6h;100%
at 135℃; Yield given;
2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

N,N-Dimethyl-N'-(pyrrolidon-2-yl-1-acetyl)formamidine
92884-66-7

N,N-Dimethyl-N'-(pyrrolidon-2-yl-1-acetyl)formamidine

A

2-oxo-1-pyrrolidine acetamide
7491-74-9

2-oxo-1-pyrrolidine acetamide

B

N,N-dimethyl-N'-homoveratrylformamidine
61945-49-1

N,N-dimethyl-N'-homoveratrylformamidine

Conditions
ConditionsYield
In benzene for 4h; Ambient temperature;A 100%
B n/a
In benzene for 4h; Ambient temperature;
2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

acetyl chloride
75-36-5

acetyl chloride

N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide
6275-29-2

N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
With triethylamine In dichloromethane at 0 - 26℃; Temperature;100%
With triethylamine In dichloromethane at 21℃; for 3h;97.7%
2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

formic acid ethyl ester
109-94-4

formic acid ethyl ester

N-[2-(3,4-dimethoxyphenyl)ethyl]formamide
14301-36-1

N-[2-(3,4-dimethoxyphenyl)ethyl]formamide

Conditions
ConditionsYield
at 70℃; for 20h;100%
at 70℃;100%
Reflux;99%

120-20-7Related news

The effect of mescaline, 3,4-Dimethoxyphenethylamine (cas 120-20-7) and 2,5-dimethoxy-4-methylamphetamine on rat plasma prolactin: Evidence for serotonergic mediation09/05/2019

Mescaline, 3,4-dimethoxyphenethylamine (DMPEA) or 2,5-dimethoxy-4-methylamphetamine (DOM) was administered to male Sprague-Dawley rats, alone or in combination with para-chlorophenylalanine (PCPA), an inhibitor of serotonin (5-HT) synthesis, or methysergide, a 5-HT receptor blocker. All three co...detailed

A sensitive and specific thin-layer chromatographic method for the identification of 3,4-Dimethoxyphenethylamine (cas 120-20-7) in urine samples09/01/2019

Procedures for the separation and quantitative determination of 3,4-dimethoxyphenethylamine as the isothiocyanate derivative are given and the thin-layer chromatographic properties of 3,4-dimethoxyphenethylamine isothiocyanate are described. The sensitivity of this method for qualitative identif...detailed

NotesEffects of 3,4-Dimethoxyphenethylamine (cas 120-20-7) Derivatives on Monoamine Oxidase08/28/2019

The cactus alkaloid 3,4-dimethoxyphenethylamine and its naturally occurring Al-methylated homologs inhibited the deamination of tyramine and tryptamine by rat brain monoamine oxidase. In contrast, the β-hydroxylated derivatives of this series failed to inhibit the action of monoamine oxidase on...detailed

120-20-7Relevant articles and documents

-

Kindler,Brandt

, p. 478,482 (1935)

-

Pathway-directed screen for inhibitors of the bacterial cell elongation machinery

Buss, Jackson A.,Baidin, Vadim,Welsh, Michael A.,Flores-Kim, Josué,Cho, Hongbaek,McKay Wood,Uehara, Tsuyoshi,Walker, Suzanne,Kahne, Daniel,Bernhardta, Thomas G.

, (2019)

New antibiotics are needed to combat the growing problem of resistant bacterial infections. An attractive avenue toward the discovery of such next-generation therapies is to identify novel inhibitors of clinically validated targets, like cell wall biogenesis. We have therefore developed a pathway-directed whole-cell screen for small molecules that block the activity of the Rod system of Escherichia coli. This conserved multiprotein complex is required for cell elongation and the morphogenesis of rod-shaped bacteria. It is composed of cell wall synthases and membrane proteins of unknown function that are organized by filaments of the actin-like MreB protein. Our screen takes advantage of the conditional essentiality of the Rod system and the ability of the beta-lactam mecillinam (also known as amdinocillin) to cause a toxic malfunctioning of the machinery. Rod system inhibitors can therefore be identified as molecules that promote growth in the presence of mecillinam under conditions permissive for the growth of Rod– cells. A screen of 690,000 compounds identified 1,300 compounds that were active against E. coli. Pathway-directed screening of a majority of this subset of compounds for Rod inhibitors successfully identified eight analogs of the MreB antagonist A22. Further characterization of the A22 analogs identified showed that their antibiotic activity under conditions where the Rod system is essential was strongly correlated with their ability to suppress mecillinam toxicity. This result combined with those from additional biological studies reinforce the notion that A22-like molecules are relatively specific for MreB and suggest that the lipoprotein transport factor LolA is unlikely to be a physiologically relevant target as previously proposed.

-

Ahl,Reichstein

, p. 366,374 (1944)

-

Synthesis and Functional Characterization of 2-(2,5-Dimethoxyphenyl)-N-(2-fluorobenzyl)ethanamine (25H-NBF) Positional Isomers

Pottie, Eline,Kupriyanova, Olga V.,Shevyrin, Vadim A.,Stove, Christophe P.

, p. 1667 - 1673 (2021/05/31)

Serotonergic psychedelics, substances exerting their pharmacological action through activation of the serotonin 2A receptor (5-HT2AR), have continuously comprised a substantial fraction of the over 1000 reported New Psychoactive Substances (NPS) so far. Within this category, N-benzyl derived phenethylamines, such as NBOMes and NBFs, have shown to be of particular relevance. As these substances remain incompletely characterized, this study aimed at synthesizing positional isomers of 25H-NBF, with two methoxy groups placed on different positions of the phenyl group of the phenethylamine moiety. These isomers were then functionally characterized in an in vitro bioassay monitoring the recruitment of β-Arrestin 2 to the 5-HT2AR through luminescent readout via the NanoBiT technology. The obtained results provide insight into the optimal substitution pattern of the phenyl group of the phenethylamine moiety of N-benzyl derived substances, a feature so far mostly explored in the phenethylamines underived at the N-position. In the employed bioassay, the most potent substances were 24H-NBF (EC50 value of 158 nM), 26H-NBF (397 nM), and 25H-NBF (448 nM), with 23H-NBF, 35H-NBF, and 34H-NBF yielding μM EC50 values. A similar ranking was obtained for the compounds' efficacy: Taking as a reference LSD (lysergic acid diethylamide), 24H-, 26H-, and 25H-NBF had an efficacy of 106-107%, followed by 23H-NBF (96.1%), 34H-NBF (75.2%), and 35H-NBF (58.9%). The stronger activity of 24H-, 25H-, and 26H-NBF emphasizes the important role of the methoxy group at position 2 of the phenethylamine moiety for the in vitro functionality of NBF substances.

Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation

Henry, Martyn C.,Senn, Hans Martin,Sutherland, Andrew

, p. 346 - 364 (2019/01/08)

A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.

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