2-(1-methyl-1H-indol-3-yl)ethanamine

Base Information

• Chemical Name: 2-(1-methyl-1H-indol-3-yl)ethanamine
• CAS No.: 7518-21-0
• Molecular Formula: C11H14N2
• Molecular Weight: 174.246
• European Community (EC) Number: 231-377-1
• DSSTox Substance ID: DTXSID80991164
• Nikkaji Number: J307.858B
• Wikidata: Q27216239
• ChEMBL ID: CHEMBL3330641
• Mol file: 7518-21-0.mol

Synonyms:7518-21-0;1-METHYLTRYPTAMINE;2-(1-methyl-1H-indol-3-yl)ethanamine;2-(1-methylindol-3-yl)ethanamine;N-Methylisotryptamine;2-(1-METHYL-1H-INDOL-3-YL)ETHAN-1-AMINE;CHEMBL3330641;1-Methyl-1H-indole-3-ethylamine;EINECS 231-377-1;1H-Indole-2-ethanamine, 1-methyl-;BRN 0473426;3-(2-AMINOETHYL)-1-METHYLINDOLE;Tryptamine, 1-methyl-;Oprea1_757922;1-Methyltryptamine, free base;SCHEMBL332959;DTXSID80991164;1-Methyl-1H-indole 3-ethanamine;CHEBI:125627;2-(1-methyl-3-indolyl)ethanamine;BBL036339;BDBM50025215;MFCD00057093;STK367793;VT1228;AKOS000276207;MB00487;1-Methyltryptamine, >=95.0% (GC);1-METHYL-1H-INDOLE-3-ETHANAMINE;2-(1-methyl-1H-indol-3-yl)-ethylamine;AS-54752;LS-82293;FT-0693777;EN300-139143;M-4645;5-22-10-00042 (Beilstein Handbook Reference);BRD-K74773935-001-01-6;Q27216239;F2106-0181;55FC1B01-ABF5-490D-A277-3CF781E25C03;1-Methyl-3-(2-aminoethyl)indole, 1-Methyl-1H-indole-3-ethanamine, 2-(1-Methyl-1H-indol-3-yl)ethylamine, N1-Methyltryptamine;1ES

Chemical Property of 2-(1-methyl-1H-indol-3-yl)ethanamine

Chemical Property:

• Boiling Point: 330.3 °C at 760 mmHg
• Flash Point: 153.6 °C
• PSA: 30.95000
• Density: 1.09 g/cm³
• LogP: 2.37980
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 174.115698455
• Heavy Atom Count: 13
• Complexity: 170

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-(1-Methylindol-3-yl)ethanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C2=CC=CC=C21)CCN

Technology Process of 2-(1-methyl-1H-indol-3-yl)ethanamine

There total 27 articles about 2-(1-methyl-1H-indol-3-yl)ethanamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

tryptamine (61-54-1) + tetramethylammonium fluoride (373-68-2) → 2-(1-methyl-1H-indol-3-yl)ethylamine (7518-21-0)

Guidance literature:

In toluene; at 100 ℃; for 12h; chemoselective reaction;

DOI:10.1021/acs.orglett.9b04400

Reference yield: 85.0%

tert-butyl [2-(1-methyl-1H-indol-3-yl)ethyl]carbamate (919787-22-7) → 2-(1-methyl-1H-indol-3-yl)ethylamine (7518-21-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 1h; Concentration;

Reference yield: 74.0%

tryptamine (61-54-1) + methyl iodide (74-88-4) → 2-(1-methyl-1H-indol-3-yl)ethylamine (7518-21-0)

Guidance literature:

tryptamine; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.833333h;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃;

DOI:10.1002/ejoc.200900820

upstream raw materials:

tryptamine

methyl iodide

1-methyl-1H-indole-3-acetonitrile

3-(2-amino-ethyl)-1-methyl-indole-2-carboxylic acid

Downstream raw materials:

o-tolyl-acetic acid-[2-(1-methyl-indol-3-yl)-ethylamide]

N-[2-(1-methyl-indol-3-yl)-ethyl]-benzamide

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

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

Refernces

• 1、 Outin, Johanne,Quellier, Pauline,Bélanger, Guillaume. "Sequential One-Pot Vilsmeier-Haack and Organocatalyzed Mannich Cyclizations to Functionalized Benzoindolizidines and Benzoquinolizidines". . p. 4712 - 4729. Retrieved 2020/03/30.
• 2、 Hock, Katharina J.,Knorrscheidt, Anja,Hommelsheim, Renè,Ho, Junming,Weissenborn, Martin J.,Koenigs, Rene M.. "Tryptamine Synthesis by Iron Porphyrin Catalyzed C?H Functionalization of Indoles with Diazoacetonitrile". . p. 3630 - 3634. Retrieved 2019/02/13.