2-Methylindole-3-ethylamine supplier

Name
2-Methylindole-3-ethylamine
EINECS 220-347-3
CAS No. 2731-06-8
Article Data42
CAS DataBase
Density 1.126 g/cm³
Solubility
Melting Point 106.0 to 110.0 °C
Formula C₁₁H₁₄N₂
Boiling Point 353 °C at 760 mmHg
Molecular Weight 174.246
Flash Point 194.4 °C
Transport Information
Appearance Brown solid
Safety
Risk Codes Xi:;
Molecular Structure
Hazard Symbols Xi
Synonyms Indole,3-(2-aminoethyl)-2-methyl- (6CI,7CI,8CI);2-Methyltryptamine;
PSA 41.81000
LogP 2.67780

Synthetic route

: 5891-21-4
5-chloro-2-pentanone

: 100-63-0
phenylhydrazine

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
In ethanol at 80℃; for 4h;	82%
In ethanol at 80℃; for 4h;	80%
In ethanol; water at 75 - 150℃; for 0.333333h; Microwave irradiation;	76%

: 39760-01-5
N-(2-(2-methyl-1H-indol-3-yl)ethyl)acetamide

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
With ammonium bromide; ethylenediamine at 100℃; for 7h; Microwave irradiation;	78%

: 2-amino-1-(2-methyl-1H-indol-3-yl)ethan-1-one

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
With triethylsilane In acetonitrile at 20 - 30℃;	76.6%

: 1353013-70-3
2,2,2-trifluoro-N-(2-(2-methyl-1H-indol-3-yl)ethyl)acetamide

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
With water; potassium carbonate In methanol for 2h; Reflux;	75%

: 765-43-5
Cyclopropyl methyl ketone

: 100-63-0
phenylhydrazine

A: 2731-06-8
2-methyltryptamine

B: 74204-92-5
3-methyl-1-phenyl-1,4,5,6-tetrahydropyridazine

Conditions

Conditions	Yield
With ammonium iodide In acetonitrile for 16h; Reflux;	A 49% B 34%

...Expand

: 120-72-9
indole

: 1016-47-3
N-Acetyltryptamine

A: 2731-06-8
2-methyltryptamine

B: 518-06-9
tris(1H-indol-3-yl)methane

C: indole trimer

D: 122709-57-3
6-<(o-aminophenyl)methyl>-5,11-dihydroindolo<3,2-b>carbazole

: 122709-55-1, 122709-56-2
(2R,3'R)-2-(1H-Indol-3-yl)-2'-methyl-1,2,4',5'-tetrahydro-spiro[indole-3,3'-pyrrole]

: 122709-55-1, 122709-56-2
(2S,3'R)-2-(1H-Indol-3-yl)-2'-methyl-1,2,4',5'-tetrahydro-spiro[indole-3,3'-pyrrole]

Conditions

Conditions	Yield
With trichlorophosphate In acetonitrile for 0.25h; Mechanism; Product distribution; Heating; labelling experiments;	A 9.6% B 0.8% C n/a D 3.5% E n/a F n/a

...Expand

: 120-72-9
indole

: 1016-47-3
N-Acetyltryptamine

A: 2731-06-8
2-methyltryptamine

B: 518-06-9
tris(1H-indol-3-yl)methane

: 122709-55-1, 122709-56-2
(2R,3'R)-2-(1H-Indol-3-yl)-2'-methyl-1,2,4',5'-tetrahydro-spiro[indole-3,3'-pyrrole]

: 122709-55-1, 122709-56-2
(2S,3'R)-2-(1H-Indol-3-yl)-2'-methyl-1,2,4',5'-tetrahydro-spiro[indole-3,3'-pyrrole]

Conditions

Conditions	Yield
With trichlorophosphate In acetonitrile for 0.25h; Heating; Further byproducts given. Yields of byproduct given;	A 9.6% B 0.8% C n/a D n/a
With trichlorophosphate In acetonitrile for 0.25h; Heating; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;	A 9.6% B 0.8% C n/a D n/a

...Expand

: 4071-16-3
2-(2-methyl-1H-indol-3-yl)acetonitrile

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
With ethanol; sodium

: 104296-24-4
2-Methyl-3-(2-nitroethyl)-1H-indole

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
With ethanol; nickel Hydrogenation;
With hydrogen; palladium on activated charcoal In methanol for 0.5h; Ambient temperature;

: dibenzyl-[2-(2-methyl-indol-3-yl)-ethyl]-amine

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
With palladium; acetic acid Hydrogenation;

: 1080-83-7
2-methyl-1H-indolyl-3-α-oxoacetamide

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In tetrahydrofuran Heating;
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h; Heating / reflux;

: 122709-55-1, 122709-56-2
2-(1H-Indol-3-yl)-2'-methyl-1,2,4',5'-tetrahydro-spiro[indole-3,3'-pyrrole]

A: 120-72-9
indole

B: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
With hydrogenchloride for 0.5h; Yield given;

: 56365-56-1
α-methyl-β-(β-bromoethyl)indole

aqueous methanol. NH3: aqueous methanol. NH3

: 2731-06-8
2-methyltryptamine

: 2826-91-7, 122631-40-7
(E)-2-methyl-3-(2-nitrovinyl)-1H-indole

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran
Multi-step reaction with 2 steps 1: 94.5 percent / H2 / tris(triphenylphosphine)rhodium(I) chloride / benzene / 20 h / 50 °C / 7500.6 Torr 2: H2 / Pd/C / methanol / 0.5 h / Ambient temperature View Scheme
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;

: 95-20-5
2-methyl-1H-indole

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: POCl3 2: AcOH 3: LiAH4 / tetrahydrofuran View Scheme
Multi-step reaction with 3 steps 1: diethyl ether / Heating 2: NH3 / dioxane 3: lithium aluminum hydride / tetrahydrofuran / Heating View Scheme
Multi-step reaction with 3 steps 1: 80.4 percent / CF3COOH / CH2Cl2 / 1) 0 deg C, 2.5 h, 2) rt, 20 h 2: 94.5 percent / H2 / tris(triphenylphosphine)rhodium(I) chloride / benzene / 20 h / 50 °C / 7500.6 Torr 3: H2 / Pd/C / methanol / 0.5 h / Ambient temperature View Scheme

: 5416-80-8
2-methyl-1H-indole-3-carbaldehyde

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: AcOH 2: LiAH4 / tetrahydrofuran View Scheme
Multi-step reaction with 3 steps 1: ammonium acetate 2: sodium tris(acetoxy)borohydride / tetrahydrofuran 3: palladium 10% on activated carbon; ammonium formate / methanol View Scheme
Multi-step reaction with 2 steps 1: ammonium acetate / 2 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 36 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: ammonium acetate / 1.5 h / Reflux; Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 36 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: ammonium acetate / 3 h / 100 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C View Scheme

: 22980-10-5
(2-methyl-3-indolyl)glyoxyloyl chloride

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NH3 / dioxane 2: lithium aluminum hydride / tetrahydrofuran / Heating View Scheme
Multi-step reaction with 2 steps 1: aq.NH3 2: LiAlH4 View Scheme

: 95-20-5
2-methyl-1H-indole

red phosphorus: red phosphorus

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 2: aq.NH3 3: LiAlH4 View Scheme

: 25576-63-0
Desoxy-dinor-9-methyl-eserolin

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
In ethanol at 20℃; Reflux;

: 56365-56-1
α-methyl-β-(β-bromoethyl)indole

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
Stage #1: α-methyl-β-(β-bromoethyl)indole With potassium phtalimide Stage #2: With hydrazine

: 2826-91-7
C11H10N2O2

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride / tetrahydrofuran 2: palladium 10% on activated carbon; ammonium formate / methanol View Scheme
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 36h; Inert atmosphere;
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 36h; Inert atmosphere;

: C11H12N2

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
With palladium 10% on activated carbon; ammonium formate In methanol

: 38693-08-2
2-chloro-1-(2-methyl-1H-indol-3-yl)ethan-1-one

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 2 h / 85 °C 2: methylamine / ethanol; water / 2 h / 85 °C 3: triethylsilane / acetonitrile / 20 - 30 °C View Scheme

: 2-[2-(2-methyl-1H-indol-3-yl)-2-oxoethyl]isoindoline-1,3-dione

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methylamine / ethanol; water / 2 h / 85 °C 2: triethylsilane / acetonitrile / 20 - 30 °C View Scheme

: (S)-2-amino-3-(2-methyl-1H-indol-3-yl)propanoic acid

: 2731-06-8
2-methyltryptamine

Conditions

Conditions	Yield
With Ruminococcus gnavus L-tryptophan decarboxylase In aq. phosphate buffer for 4h; pH=8.0; Catalytic behavior; Enzymatic reaction;

: 2731-06-8
2-methyltryptamine

: 87-13-8
diethyl 2-ethoxymethylenemalonate

: 2-{[2-(2-methyl-1H-indol-3-yl)-ethylamino]-methylene}-malonic acid diethyl ester

Conditions

Conditions	Yield
In ethanol	95%

: 2731-06-8
2-methyltryptamine

: 7560-50-1, 71093-79-3, 58045-41-3
methyl (2E)-3-(4-formylphenyl)acrylate

: 441741-66-8
(E)-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]acrylic acid methyl ester hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-methyltryptamine; methyl (2E)-3-(4-formylphenyl)acrylate In methanol at 25 - 35℃; for 1h; Stage #2: With hydrogenchloride In ethanol; water at 0 - 5℃; for 1h; pH=3 - 4; Solvent; Temperature;	90.4%
Stage #1: 2-methyltryptamine; methyl (2E)-3-(4-formylphenyl)acrylate With sodium tetrahydroborate In methanol at 0℃; Stage #2: With hydrogenchloride In water

: 2731-06-8
2-methyltryptamine

: 24424-99-5
di-tert-butyl dicarbonate

: tert-butyl (2-(2-methyl-1H-indol-3-yl)ethyl)carbamate

Conditions

Conditions	Yield
In 1,4-dioxane at 20℃; for 16h;	90%
With sodium hydroxide In dichloromethane; ethyl acetate at 0 - 20℃; for 0.5h;

: 2731-06-8
2-methyltryptamine

: 470-17-7
isoalantolactone

: 1415809-59-4
(11R)-13-(2-methyltryptamino)-11,13-dihydroisoalantolactone ((3R,3aR,4aR,8aR,9aR)-3-{[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl}-8a-methyl-5-methylidenedecahydronaphtho[2,3-b]furan-2-one)

Conditions

Conditions	Yield
In methanol at 20℃; Michael Addition;	83%

: 2731-06-8
2-methyltryptamine

: 5728-32-5
4-(2-methoxyphenyl)benzoic acid

: 2’-methoxy-N-(2-(2-methyl-1H-indol-3-yl)ethyl)-[1,1‘-biphenyl]-4-carboxamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 10h;	83%

: 2731-06-8
2-methyltryptamine

: 66885-68-5
(E)-p-formylcinnamic acid

: 960058-93-9
(E)-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)acrylic acid

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran; methanol; 1,2-dichloro-ethane	81%
With sodium cyanoborohydride; acetic acid In methanol	70%
With sodium cyanoborohydride; acetic acid In methanol

: 2731-06-8
2-methyltryptamine

: 1609031-15-3
(E)-3-(3,4-bis(2-hydroxyethoxy)phenyl)acrylic Acid

: 1609030-89-8
(E)-3-(3,4-bis(2-hydroxyethoxy)phenyl)-N-(2-(2-methyl-1H-indol-3-yl)ethyl)acrylamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 8h;	80%

: 2731-06-8
2-methyltryptamine

: 5-(4-acetamidophenyl)picolinic acid

: 5-(4-acetamidophenyl)-N-(2-(2-methyl-1H-indol-3-yl)ethyl)picolinamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 10h;	80%

: 2731-06-8
2-methyltryptamine

: 32315-10-9
bis(trichloromethyl) carbonate

: 24036-91-7
19-nor-Δ1,3,5(10)-22α-spirostatriene-3-ol

: (22R,25R)-3β-(2-methyl-1H-indole-3-ethylamine-carboxylate)-1,3,5(10)-trien-20α-spirostan

Conditions

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; 19-nor-Δ1,3,5(10)-22α-spirostatriene-3-ol With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-methyltryptamine In dichloromethane at 20℃; for 3h; Inert atmosphere;	79%

...Expand

: 2731-06-8
2-methyltryptamine

: 2905-24-0
3-Bromobenzenesulfonyl chloride

: 1622137-40-9
3-bromo-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzenesulfonamide

Conditions

Conditions	Yield
With pyridine In acetonitrile at 20℃; for 2h; Inert atmosphere;	76%
With pyridine In acetonitrile at 20℃; for 2h; Inert atmosphere;	76%

: 2731-06-8
2-methyltryptamine

: 24424-99-5
di-tert-butyl dicarbonate

: C26H38N2O6

Conditions

Conditions	Yield
With dmap In acetonitrile at 20℃; Inert atmosphere; Sealed tube;	76%

: 2731-06-8
2-methyltryptamine

: C14H13NO4

: 5-(3,5-dimethoxyphenyl)-N-(2-(2-methyl-1H-indol-3-yl)ethyl)picolinamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 10h;	76%

: 2731-06-8
2-methyltryptamine

: 2243-53-0
styrylacetic acid

: (E)-N-(2-(2-methyl-1H-indol-3-yl)ethyl)-4-phenylbut-3-enamide

Conditions

Conditions	Yield
Stage #1: styrylacetic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.0833333h; Stage #2: 2-methyltryptamine In dichloromethane at 20℃;	75%

: 2731-06-8
2-methyltryptamine

: C13H11NO3

: 6-(3-methoxyphenyl)-N-(2-(2-methyl-1H-indol-3-yl)ethyl)nicotinamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 10h;	74%

: 2731-06-8
2-methyltryptamine

: 20577-61-1
methyl 2,4-dioxopentanoate

: 1571-08-0
methyl 4-formylbenzoate

: 1560894-05-4, 1569976-80-2, 1569976-83-5
methyl 4-(3-acetyl-4-hydroxy-1-(2-(2-methyl-1H-indol-3-yl)-ethyl)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)benzoate

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In 1,4-dioxane at 20℃; for 12h;	73%

...Expand

: 2731-06-8
2-methyltryptamine

: 1571-08-0
methyl 4-formylbenzoate

: methyl 4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)benzoate

Conditions

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol	72%

: 2731-06-8
2-methyltryptamine

: 29051-44-3
6-phenylpyridine-3-carboxylic acid

: N-(2-(2-methyl-1H-indol-3-yl)ethyl)-6-phenylnicotinamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 10h;	71%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 10h;	71%

: 2731-06-8
2-methyltryptamine

: 51359-78-5
4-(bromomethyl)benzaldehyde

: 4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]benzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; Temperature; Inert atmosphere;	70%

: 2731-06-8
2-methyltryptamine

: 505082-91-7
6-(2-fluorophenyl)pyridine-3-carboxylic acid

: 6-(2-fluorophenyl)-N-(2-(2-methyl-1H-indol-3-yl)ethyl)nicotinamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 10h;	70%

: 2731-06-8
2-methyltryptamine

: 52178-50-4
Methyl 3-formylbenzoate

: methyl 3-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)benzoate

Conditions

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol	70%

: 2731-06-8
2-methyltryptamine

: 6-(2-methoxyphenyl)nicotinic acid

: 6-(2-methoxyphenyl)-N-(2-(2-methyl-1H-indol-3-yl)ethyl)nicotinamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 10h;	69%

: 2731-06-8
2-methyltryptamine

: 41624-92-4
methyl 8-chloro-8-oxooctanoate

: methyl 8-(((2-methyl-1H-indol-3-yl)ethyl)amino)-8-oxooctanoate

Conditions

Conditions	Yield
With potassium carbonate In dichloromethane for 2h;	68%

: 2731-06-8
2-methyltryptamine

: methyl (E)-3-(2-formylpyrimidin-5-yl)acrylate

: methyl-(E)-3-(2-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)pyrimidin-5-yl)acrylate

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; triethylamine In 1,2-dichloro-ethane at 20℃; for 15h; Inert atmosphere;	68%

2-Methylindole-3-ethylamine Chemical Properties

IUPAC Name: 2-(2-Methyl-1H-indol-3-yl)ethanamine
Synonyms of of 1H-Indole-3-ethanamine,2-methyl- (CAS NO.2731-06-8): EINECS 220-347-3 ; 2-Methyl-1H-indole-3-ethylamine
CAS NO: 2731-06-8
Molecular Formula: C₁₁H₁₄N₂
Molecular Weight: 174.2423
Molecular Structure:

H bond acceptors: 2
H bond donors: 3
Freely Rotating Bonds: 3
Polar Surface Area: 8.17 Å²
Index of Refraction: 1.65
Molar Refractivity: 56.43 cm³
Molar Volume: 154.6 cm3
Surface Tension: 51.3 dyne/cm
Density of 1H-Indole-3-ethanamine,2-methyl- (CAS NO.2731-06-8): 1.126 g/cm3
Flash Point: 194.4 °C
Enthalpy of Vaporization: 59.79 kJ/mol
Boiling Point: 353 °C at 760 mmHg
Vapour Pressure: 3.69E-05 mmHg at 25°C

2-Methylindole-3-ethylamine Safety Profile

Hazard Codes: Xi
HazardClass: IRRITANT

Product Name

2-Methylindole-3-ethylamine

Synthetic route

2-Methylindole-3-ethylamine Chemical Properties

2-Methylindole-3-ethylamine Safety Profile

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