Product Name

  • Name

    3-(2-Aminoethyl)-6-methoxyindole

  • EINECS 222-778-2
  • CAS No. 3610-36-4
  • Article Data19
  • CAS DataBase
  • Density 1.172 g/cm3
  • Solubility Moderately soluble in water
  • Melting Point 146-147 °C(lit.)
  • Formula C11H14N2O
  • Boiling Point 380.031 °C at 760 mmHg
  • Molecular Weight 190.245
  • Flash Point 183.636 °C
  • Transport Information
  • Appearance Light yellow-brown needles.
  • Safety 45-36/37/39-26
  • Risk Codes 43-34
  • Molecular Structure Molecular Structure of 3610-36-4 (3-(2-Aminoethyl)-6-methoxyindole)
  • Hazard Symbols CorrosiveC
  • Synonyms Indole,3-(2-aminoethyl)-6-methoxy- (6CI,7CI,8CI);2-(6-Methoxyindol-3-yl)ethylamine;6MOT;Ba 2808;2-(6-Methoxy-1H-indol-3-yl)ethylamine;
  • PSA 51.04000
  • LogP 2.37800

Synthetic route

2-carboxyethyl-3-(2-phthalimidoethyl)-6-methoxyindole
282103-23-5

2-carboxyethyl-3-(2-phthalimidoethyl)-6-methoxyindole

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
Stage #1: 2-carboxyethyl-3-(2-phthalimidoethyl)-6-methoxyindole With potassium hydroxide In water for 3h; Heating;
Stage #2: With hydrogenchloride In water for 10h; Heating;		90%
C25H42N2O3Si

C25H42N2O3Si

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
Stage #1: C25H42N2O3Si With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: With cesium fluoride In tetrahydrofuran; methanol; toluene at 20℃; for 6h; Inert atmosphere;		58%
2-(6-methoxy-1H-indol-3-yl)acetonitrile
23084-35-7

2-(6-methoxy-1H-indol-3-yl)acetonitrile

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
With methanol; ammonia; nickel under 73550.8 Torr; Hydrogenation;
With lithium aluminium tetrahydride; diethyl ether
With ethanol; sodium
2-(6-methoxy-1H-indol-3-yl)-2-oxo-acetamide
103858-66-8

2-(6-methoxy-1H-indol-3-yl)-2-oxo-acetamide

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
With tetrahydrofuran; lithium aluminium tetrahydride
6-methoxytryptamine-2-carboxylic acid
20731-72-0

6-methoxytryptamine-2-carboxylic acid

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
With hydrogenchloride
6-methoxy-3-(2-nitroethyl)-1H-indole
96096-61-6

6-methoxy-3-(2-nitroethyl)-1H-indole

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol under 2585.7 Torr; for 12h;
6-methoxylindole
3189-13-7

6-methoxylindole

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 27 percent / tert-butylcatechol / xylene / 3 h / Heating
2: H2 / 10 percent Pd/C / ethanol / 12 h / 2585.7 Torr
View Scheme
Multi-step reaction with 2 steps
1: methyl magnesium iodide; diethyl ether / Behandeln des Reaktionsgemisches mit Chloracetonitril
2: sodium; ethanol
View Scheme
Multi-step reaction with 3 steps
1: acetic acid; dioxane
2: dimethyl sulfate; acetic acid; THF / Erwaermen des Reaktionsprodukts in H2O mit KCN
3: Raney nickel; NH3; methanol / 73550.8 Torr / Hydrogenation
View Scheme
Multi-step reaction with 3 steps
1: diethyl ether
2: concentrated aqueous NH3
3: LiAlH4; THF
View Scheme
Multi-step reaction with 2 steps
1.1: trichlorophosphate / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique
1.2: 2 h / 20 °C / Inert atmosphere; Schlenk technique
2.1: ammonium acetate / 2 h / 115 °C / Inert atmosphere; Schlenk technique
2.2: 3 h / 0 - 65 °C / Inert atmosphere; Schlenk technique
View Scheme
6-methoxy-3-((trimethyl-14-azaneyl)methyl)-1H-indole iodide
109507-20-2

6-methoxy-3-((trimethyl-14-azaneyl)methyl)-1H-indole iodide

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: LiAlH4; diethyl ether
View Scheme
1-(6-methoxy-1H-indol-3-yl)-N,N-dimethylmethanamine
62467-65-6

1-(6-methoxy-1H-indol-3-yl)-N,N-dimethylmethanamine

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethyl sulfate; acetic acid; THF / Erwaermen des Reaktionsprodukts in H2O mit KCN
2: Raney nickel; NH3; methanol / 73550.8 Torr / Hydrogenation
View Scheme
7-methoxy-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indol-1-one
26579-69-1

7-methoxy-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indol-1-one

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq.-ethanolic KOH
2: aqueous HCl
View Scheme
(6-methoxy-1H-indol-3-yl)(oxo)acetyl chloride
68104-22-3

(6-methoxy-1H-indol-3-yl)(oxo)acetyl chloride

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated aqueous NH3
2: LiAlH4; THF
View Scheme
2,β-Dinitro-4-methoxy-styrol
99459-34-4

2,β-Dinitro-4-methoxy-styrol

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethyl acetate; palladium/charcoal; ethanol / Hydrogenation.Reagens 4: Essigsaeure
2: diethyl ether
3: concentrated aqueous NH3
4: LiAlH4; THF
View Scheme
6-methoxy-3-(2-nitrovinyl)indole
91138-34-0

6-methoxy-3-(2-nitrovinyl)indole

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃;
6-methoxylindole
3189-13-7

6-methoxylindole

1-dimethylamino-2-nitroethene
73430-27-0, 87446-70-6, 1190-92-7

1-dimethylamino-2-nitroethene

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
Stage #1: 6-methoxylindole; 1-dimethylamino-2-nitroethene In dichloromethane; trifluoroacetic acid at 20℃; for 2h;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at -78℃;
6-methoxy-1H-indole-3-carbaldehyde
70555-46-3

6-methoxy-1H-indole-3-carbaldehyde

nitromethane
75-52-5

nitromethane

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
Stage #1: 6-methoxy-1H-indole-3-carbaldehyde; nitromethane With ammonium acetate at 115℃; for 2h; Henry Nitro Aldol Condensation; Inert atmosphere; Schlenk technique;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 65℃; for 3h; Inert atmosphere; Schlenk technique;		270 mg
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

C18H17ClN2O
1120500-26-6

C18H17ClN2O

Conditions
ConditionsYield
With sodium sulfate In dichloromethane at 23℃; for 3h; Inert atmosphere; Sealed tube;100%
With sodium sulfate In dichloromethane at 23℃; for 3h; Inert atmosphere;
4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

(E)-4-(((2-(6-methoxy-1H-indol-3-yl)ethyl)imino)methyl)benzonitrile

(E)-4-(((2-(6-methoxy-1H-indol-3-yl)ethyl)imino)methyl)benzonitrile

Conditions
ConditionsYield
With sodium sulfate In dichloromethane at 23℃; for 3h; Inert atmosphere; Sealed tube;100%
4-formylbenzonitrile-α-d1
109635-36-1

4-formylbenzonitrile-α-d1

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

(E)-4-(((2-(6-methoxy-1H-indol-3-yl)ethyl)imino)methyl-[2H])benzonitrile

(E)-4-(((2-(6-methoxy-1H-indol-3-yl)ethyl)imino)methyl-[2H])benzonitrile

Conditions
ConditionsYield
With sodium sulfate In dichloromethane at 23℃; for 3h; Inert atmosphere; Sealed tube;100%
Glyoxilic acid
298-12-4

Glyoxilic acid

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

7-methoxy-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid
108850-87-9

7-methoxy-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In water; ethyl acetate at 20℃; for 24h; pH=5; Pictet-Spengler Synthesis;99%
With potassium hydroxide In water at 20℃; for 12h; pH=3 - 4; Pictet-Spengler reaction;
With NaOAc buffer In ethyl acetate for 48h; pH=4.5;
2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

Trifluoroacetaldehyde ethyl hemiacetal
433-27-2

Trifluoroacetaldehyde ethyl hemiacetal

7-methoxy-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole
126260-60-4

7-methoxy-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole

Conditions
ConditionsYield
at 110 - 120℃; for 5h;98.4%
With hydrogenchloride In methanol at 20℃; Pictet-Spengler cyclisation;
1,1-dimethoxyethane
534-15-6

1,1-dimethoxyethane

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride
40959-16-8

7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

Conditions
ConditionsYield
Stage #1: 1,1-dimethoxyethane; 2-(6-methoxy-1H-indol-3-yl)ethanamine With trifluoroacetic acid In 1,2-dichloro-ethane at 110℃; for 0.05h; Pictet-Spengler Synthesis; Sealed tube; Microwave irradiation;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃;		98%
4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

(R)-4-(7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)benzonitrile

(R)-4-(7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)benzonitrile

Conditions
ConditionsYield
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide; benzoic acid In toluene at 23℃; for 24h; Pictet-Spengler Synthesis; Inert atmosphere; Sealed tube; enantioselective reaction;98%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

trifluoroacetic acid
76-05-1

trifluoroacetic acid

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

1-(pyridin-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole trifluoroacetate

1-(pyridin-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole trifluoroacetate

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 110℃; for 0.0833333h; Pictet-Spengler Synthesis; Sealed tube; Microwave irradiation;97%
...Expand
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

C16H22N2O3
1159000-30-2

C16H22N2O3

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 12h;96%
benzaldehyde
100-52-7

benzaldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

7-methoxy-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

7-methoxy-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

Conditions
ConditionsYield
Stage #1: benzaldehyde; 2-(6-methoxy-1H-indol-3-yl)ethanamine With trifluoroacetic acid In 1,2-dichloro-ethane at 110℃; for 0.183333h; Pictet-Spengler Synthesis; Sealed tube; Microwave irradiation;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃;		95%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

(R)-1-(4-chlorophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
1120500-34-6

(R)-1-(4-chlorophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Conditions
ConditionsYield
With 1,1'-(2S,2'S)-1,1'-(4,10-dimethyl-1,4,7,10-tetraazacyclododecane-1,7-diyl)bis(3-methyl-1-oxobutane-2,1-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl)thiourea); 4-methoxybenzoic acid In toluene at 20℃; for 72h; Pictet-Spengler Synthesis; enantioselective reaction;93%
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide; benzoic acid In toluene at 23℃; for 66h; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;78%
3,4,5-trimethoxybenzoylformic acid
88755-16-2

3,4,5-trimethoxybenzoylformic acid

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

N-(2-(6-methoxy-1H-indol-3-yl)ethyl)-2-(3,4,5-trimethoxyphenyl)-2-oxoacetamide

N-(2-(6-methoxy-1H-indol-3-yl)ethyl)-2-(3,4,5-trimethoxyphenyl)-2-oxoacetamide

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole93%
acetaldehyde
75-07-0

acetaldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

tetrahydroharmine
486-93-1, 17019-01-1

tetrahydroharmine

Conditions
ConditionsYield
With hydrogenchloride In water at 40℃; for 6h; Pictet-Spengler Synthesis;92%
With sulfuric acid In water at 110℃; for 0.333333h;63%
With sulfuric acid
Stage #1: 2-(6-methoxy-1H-indol-3-yl)ethanamine With hydrogenchloride In water at 30℃;
Stage #2: acetaldehyde In water for 10h;
With acetic acid for 8h; Reflux;
isobutyraldehyde
78-84-2

isobutyraldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

(R)-1-isopropyl-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
1120500-56-2

(R)-1-isopropyl-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Conditions
ConditionsYield
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide In toluene at 23℃; for 88h; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;90%
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

(R)-1-(2-chlorophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

(R)-1-(2-chlorophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Conditions
ConditionsYield
With 1,1'-(2S,2'S)-1,1'-(4,10-dimethyl-1,4,7,10-tetraazacyclododecane-1,7-diyl)bis(3-methyl-1-oxobutane-2,1-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl)thiourea); 4-methoxybenzoic acid In toluene at 20℃; for 72h; Pictet-Spengler Synthesis; enantioselective reaction;89%
potassium cyanide
151-50-8

potassium cyanide

(1S,2R,3R,5S,6S)-3-Hydroxy-2-methoxy-6-(2-oxo-ethyl)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

(1S,2R,3R,5S,6S)-3-Hydroxy-2-methoxy-6-(2-oxo-ethyl)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

(3S,4aR,5R,6S,7S,8aR)-3-Cyano-7-hydroxy-6-methoxy-2-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-decahydro-isoquinoline-5-carboxylic acid methyl ester

(3S,4aR,5R,6S,7S,8aR)-3-Cyano-7-hydroxy-6-methoxy-2-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-decahydro-isoquinoline-5-carboxylic acid methyl ester

Conditions
ConditionsYield
With magnesium sulfate In acetonitrile for 1h; Strecker reaction;87%
...Expand
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

(R)-1-(3-bromophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
1120500-41-5

(R)-1-(3-bromophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Conditions
ConditionsYield
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide; benzoic acid In toluene at 23℃; for 19h; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;87%
With 1,1'-(2S,2'S)-1,1'-(4,10-dimethyl-1,4,7,10-tetraazacyclododecane-1,7-diyl)bis(3-methyl-1-oxobutane-2,1-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl)thiourea); 4-methoxybenzoic acid In toluene at 20℃; for 72h; Pictet-Spengler Synthesis; enantioselective reaction;84%
benzaldehyde
100-52-7

benzaldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

7-methoxy-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline
865681-22-7

7-methoxy-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 110℃; for 0.166667h; Microwave irradiation; Sealed tube;87%
potassium cyanide

potassium cyanide

C28H32O9S

C28H32O9S

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

C34H39N3O6

C34H39N3O6

Conditions
ConditionsYield
With magnesium sulfate In acetonitrile diastereoselective reaction;87%
...Expand
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

N-(2-(6-methoxy-1H-indol-3-yl)ethyl)-4-nitrobenzenesulfonamide

N-(2-(6-methoxy-1H-indol-3-yl)ethyl)-4-nitrobenzenesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20 - 30℃; for 2h; Inert atmosphere;87%
acetic anhydride
108-24-7

acetic anhydride

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

N-(2-(6-methoxy-1H-indol-3-yl)ethyl)acetamide
22375-73-1

N-(2-(6-methoxy-1H-indol-3-yl)ethyl)acetamide

Conditions
ConditionsYield
With TEA In tetrahydrofuran for 6h; Ambient temperature;86%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

(R)-7-methoxy-1-(pentan-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
1120500-58-4

(R)-7-methoxy-1-(pentan-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Conditions
ConditionsYield
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide In toluene at 23℃; for 120h; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;84%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

(R)-1-(4-bromophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
1120500-38-0

(R)-1-(4-bromophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Conditions
ConditionsYield
With 1,1'-(2S,2'S)-1,1'-(4,10-dimethyl-1,4,7,10-tetraazacyclododecane-1,7-diyl)bis(3-methyl-1-oxobutane-2,1-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl)thiourea); 4-methoxybenzoic acid In toluene at 20℃; for 72h; Pictet-Spengler Synthesis; enantioselective reaction;84%
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide; benzoic acid In toluene at 23℃; for 74h; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;79%
2-(isocyanatomethyl)-1,3-dioxolane
1467040-44-3

2-(isocyanatomethyl)-1,3-dioxolane

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

9-methoxy-5,6,11,11b-tetrahydro-1H-imidazo[1',5':1,2]pyrido[3,4-b]indol-3(2H)-one
1467040-48-7

9-methoxy-5,6,11,11b-tetrahydro-1H-imidazo[1',5':1,2]pyrido[3,4-b]indol-3(2H)-one

Conditions
ConditionsYield
Stage #1: 2-(isocyanatomethyl)-1,3-dioxolane; 2-(6-methoxy-1H-indol-3-yl)ethanamine In tetrahydrofuran at 20℃; for 7h; Pictet-Spengler Synthesis; Inert atmosphere;
Stage #2: With hydrogenchloride In methanol; water at 55℃; for 4h; Pictet-Spengler Synthesis; Inert atmosphere;		84%
N-(4-carboxybenzyl)-1-(3-chlorophenyl)-N-methylmethanaminium chloride
1605289-54-0

N-(4-carboxybenzyl)-1-(3-chlorophenyl)-N-methylmethanaminium chloride

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

4-{[(3-chlorobenzyl)(methyl)amino]methyl}-N-[2-(6-methoxy-1H-indol-3-yl)ethyl]benzamide
1317668-18-0

4-{[(3-chlorobenzyl)(methyl)amino]methyl}-N-[2-(6-methoxy-1H-indol-3-yl)ethyl]benzamide

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃;82%
isobutyraldehyde
78-84-2

isobutyraldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

1-isopropyl-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

1-isopropyl-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

Conditions
ConditionsYield
Stage #1: isobutyraldehyde; 2-(6-methoxy-1H-indol-3-yl)ethanamine With trifluoroacetic acid In 1,2-dichloro-ethane at 110℃; for 0.05h; Pictet-Spengler Synthesis; Sealed tube; Microwave irradiation;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃;		82%
isobutyraldehyde
78-84-2

isobutyraldehyde

trifluoroacetic acid
76-05-1

trifluoroacetic acid

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

1-isopropyl-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

1-isopropyl-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 110℃; for 0.05h; Pictet-Spengler Synthesis; Sealed tube; Microwave irradiation;82%
...Expand
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

(R)-1-(4-fluorophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
1120500-35-7

(R)-1-(4-fluorophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Conditions
ConditionsYield
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide; benzoic acid In toluene at 23℃; for 70h; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;81%
10-methoxy-2,2-dimethyl-2,6,7,12-tetrahydroindolo[2,3-a]quinolizin-4(3H)-one

10-methoxy-2,2-dimethyl-2,6,7,12-tetrahydroindolo[2,3-a]quinolizin-4(3H)-one

2-(6-methoxy-1H-indol-3-yl)ethanamine
3610-36-4

2-(6-methoxy-1H-indol-3-yl)ethanamine

(+)-peganumine A
1620517-85-2

(+)-peganumine A

Conditions
ConditionsYield
With (R)-2,6-bis(3,5-difluoro-4-(trifluoromethyl)phenyl)-4H-dinaphtho[2,1-d:1',2'-f][1,3,2]dithiazepine 3,3,5,5-tetraoxide In toluene at 60℃; Catalytic behavior; Solvent; Temperature; Pictet-Spengler Synthesis; Inert atmosphere; Schlenk technique; Molecular sieve; Sealed tube; enantioselective reaction;81%

6-Methoxytryptamine Chemical Properties

Molecular structure of 2-(2-Aminoethyl)-5-methoxyindole (CAS NO.3610-36-4) is:

Product Name: 2-(2-Aminoethyl)-5-methoxyindole 
CAS Registry Number: 3610-36-4
IUPAC Name: 2-(6-methoxy-1H-indol-3-yl)ethanamine
Molecular Weight: 190.24166 [g/mol]
Molecular Formula: C11H14N2O
XLogP3: 1.5
H-Bond Donor: 2
H-Bond Acceptor: 2 
Surface Tension: 50.5 dyne/cm
Density: 1.171 g/cm3
Flash Point: 183.6 °C
Enthalpy of Vaporization: 62.81 kJ/mol
Boiling Point: 380 °C at 760 mmHg
Vapour Pressure: 5.61E-06 mmHg at 25°C
Melting Point: 146-147 °C(lit.)
Storage temp.: 2-8°C
Water Solubility: moderately soluble
Product Categories: Tryptamines

6-Methoxytryptamine Safety Profile

Safty information about 2-(2-Aminoethyl)-5-methoxyindole (CAS NO.3610-36-4) is:
Hazard Codes: CorrosiveC
Risk Statements: 43-34 
R43:May cause sensitization by skin contact. 
R34:Causes burns.
Safety Statements: 45-36/37/39-26 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3

6-Methoxytryptamine Specification

 2-(2-Aminoethyl)-5-methoxyindole , its cas register number is 3610-36-4. It also can be called  EINECS 222-778-2 ;1H-Indole-3-ethanamine, 6-methoxy- ; 2-(2-Aminoethyl)-5-methoxyindole ; 2-(6-Methoxy-1H-indol-3-yl)ethanamine .It is a off-white to beige crystalline powder.
First Aid Measures:
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin: Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion: Do not induce vomiting. Get medical aid immediately.
Inhalation: Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician: Treat symptomatically and supportively.
Handling and Storage
Handling: Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage: Keep refrigerated. (Store below 4°C/39°F.) Store in a tightly closed container. Store in a dry area. Corrosives area.

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