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

Base Information

• Chemical Name: 2-(1H-indol-1-yl)ethanamine
• CAS No.: 13708-58-2
• Molecular Formula: C10H12 N2
• Molecular Weight: 160.219
• Hs Code.: 2933990090
• NSC Number: 87953
• DSSTox Substance ID: DTXSID10293224
• Nikkaji Number: J2.223.382C
• Wikidata: Q27451192
• Mol file: 13708-58-2.mol

Synonyms:2-(1H-indol-1-yl)ethanamine;13708-58-2;2-indol-1-ylethanamine;2-(1H-indol-1-yl)ethan-1-amine;[2-(1H-indol-1-yl)ethyl]amine hydrochloride;2-(INDOL-1-YL)ETHYLAMINE;[2-(1H-Indol-1-yl)ethyl]amine;NSC87953;1-(2-aminoethyl)indole;2-Indol-1-yl-ethylamine;F1386-0299;SCHEMBL1120445;DTXSID10293224;BXEFQUSYBZYTAE-UHFFFAOYSA-N;HMS1653G10;BBL030026;MFCD03643872;NSC-87953;STK501719;AKOS005172398;VS-09563;2-(1H-Indol-1-yl)ethanamine, AldrichCPR;BB 0269973;FT-0711190;EN300-236418;W-205496;Q27451192;0LH

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

Chemical Property:

• Vapor Pressure: 0.000685mmHg at 25°C
• Boiling Point: 308.3°C at 760 mmHg
• Flash Point: 140.3°C
• PSA: 30.95000
• Density: 1.11g/cm³
• LogP: 2.30030
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 160.100048391
• Heavy Atom Count: 12
• Complexity: 147

Purity/Quality:

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

2-(1H-Indol-1-yl)ethanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 25-37/38-41
• Safety Statements: 26-39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CN2CCN
• General Description: **2-(1H-Indol-1-yl)ethanamine** is a key reactant in enantioselective iso-Pictet-Spengler reactions, where it condenses with α-ketoamides in the presence of a chiral silicon Lewis acid to form 1,1-disubstituted-1,2,3,4-tetrahydropyrazino[1,2-a]indoles, an underexplored indole-based scaffold with potential medicinal chemistry applications. The reaction demonstrates high enantioselectivity and scalability, highlighting the utility of this amine in constructing complex heterocyclic frameworks.

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

There total 14 articles about 2-(1H-indol-1-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: 95.0%

1-Indolylacetonitrile (4414-73-7) → 2-indol-1-yl-ethylamine (13708-58-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 2.5h; Heating;

DOI:10.1007/BF01373544

Reference yield: 86.0%

1-cyanomethyl-3-phenylsulfonylindole (1243565-32-3) → 2-indol-1-yl-ethylamine (13708-58-2)

Guidance literature:

With Raney nickel; In tetrahydrofuran; for 5h; Reflux;

DOI:10.1007/s10593-010-0504-3

Reference yield: 74.0%

1-(2-azidoethyl)-1H-indole → 2-indol-1-yl-ethylamine (13708-58-2)

Guidance literature:

With water; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/ol203364b

upstream raw materials:

N-(2-indol-1-ylethyl)benzamide

1-Indolylacetonitrile

indole

2-chloroethanamine hydrochloride

Downstream raw materials:

S-6-(tert-butoxycarbonyl)-5,6-dihydro-6H-[1,4]diazepino[6,7,1-hi]indole

1,2,3,4,6,7-hexahydro-[1,4]diazepino[6,7,1-hi]indole

2-(2,3-dihydro-1H-indol-1-yl)ethanamine

N-(2-(1H-indol-1-yl)ethyl)-4-(diethylamino)benzamide

Refernces

Direct and highly enantioselective iso-Pictet-Spengler reactions with α-ketoamides: Access to underexplored indole core structures

10.1021/ol300922b

The study reports the development of direct, one-pot, and highly enantioselective iso-Pictet-Spengler reactions involving the condensation of either (1H-indol-4-yl)methanamine or 2-(1H-Indol-1-yl)ethanamine with various r-ketoamides, followed by the addition of a commercially available chiral silicon Lewis acid. These reactions provide access to 3,3-disubstituted-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinolines and 1,1-disubstituted-1,2,3,4-tetrahydropyrazino[1,2-a]indoles, two underexplored indole-based core structures in medicinal chemistry. The researchers optimized the reactions for different r-ketoamides, achieving high enantioselectivity and yields, demonstrating the practicality and scalability of their method.