(1H-Indol-3-yl)-1-propanamine

Base Information

• Chemical Name: (1H-Indol-3-yl)-1-propanamine
• CAS No.: 6245-89-2
• Molecular Formula: C11H14 N2
• Molecular Weight: 174.246
• Hs Code.: 2933990090
• European Community (EC) Number: 228-361-1
• DSSTox Substance ID: DTXSID00211492
• Nikkaji Number: J211.473I
• Wikidata: Q83086429
• ChEMBL ID: CHEMBL2229708
• Mol file: 6245-89-2.mol

Synonyms:6245-89-2;(1H-Indol-3-yl)-1-propanamine;3-(1H-indol-3-yl)propan-1-amine;1H-Indole-3-propylamine;1H-Indole-3-propanamine;Homotryptamine;3-(Indol-3-yl)propanamine;(1H-lndol-3-yl)-1-propanamine;EINECS 228-361-1;MFCD00130194;3-(3-aminopropyl)indole;Oprea1_526363;SCHEMBL735189;1H-Indole-3-propan-1-amine;3-(1H-indol-3-yl)propylamine;CHEMBL2229708;DTXSID00211492;3-(1H-indol-3-yl)-propylamine;BBL020229;STK386772;AKOS001476511;CS-W018622;FS-2717;FS-3765;3-(1H-Indol-3-yl)-1-propanamine #;[3-(1H-indol-3-yl)-prop-1-yl]amine;NCGC00342755-01;SY042804;FT-0732575;EN300-72181;AB01334180-02;A1-04140;F1160-0010;Z275361382

Chemical Property of (1H-Indol-3-yl)-1-propanamine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 64 °C
• Boiling Point: 353.725°C at 760 mmHg
• PKA: 17.29±0.30(Predicted)
• Flash Point: 194.877°C
• PSA: 27.82000
• Density: 1.125g/cm³
• LogP: 3.06280
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 174.115698455
• Heavy Atom Count: 13
• Complexity: 158

Purity/Quality:

99%, ^*data from raw suppliers

3-(Indol-3-yl)propanamine ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22-37/38-48
• Safety Statements: 22-26-7/8-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CCCN

Technology Process of (1H-Indol-3-yl)-1-propanamine

There total 26 articles about (1H-Indol-3-yl)-1-propanamine 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: 100.0%

3-(3-indolyl)-propanamide (5814-93-7) → Homotryptamine (6245-89-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 24h; Reflux;

DOI:10.1021/acs.jmedchem.8b00001

Reference yield: 92.0%

1H-indole-3-propiononitrile (4414-76-0) → Homotryptamine (6245-89-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 3h; Heating;

DOI:10.1021/jo000249z

Reference yield:

Indole-3-propionic acid (830-96-6) → Homotryptamine (6245-89-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1.5 h / 20 °C

1.2: 96 percent / NH₃(g) / tetrahydrofuran / 2.5 h / 20 °C

2.1: 86 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

With lithium aluminium tetrahydride; 1,1'-carbonyldiimidazole; In tetrahydrofuran;

DOI:10.1021/jm0304010

upstream raw materials:

2-[3-(3-Indolyl)propyl]isoindoline-1,3-dione

3-indol-3-yl-acrylonitrile

3-(3-indolyl)-propanamide

1H-indole-3-propiononitrile

Downstream raw materials:

2-{2-[3-(1H-indol-3-yl)propylamino]ethoxy}-6-nitrophenylamine

2-(4-dimethylamino-4-phenyl-cyclohexylidene)-N-[3-(1H-indol-3-yl)-propyl]-acetamide

N-1-[3-(1H-indol-3-yl)propyl]-4-methyl-1-benzenesulfonamide

Refernces

Catalytic asymmetric diazoacetate cyclopropanation of 1-tosyl-3- vinylindoles. A route to conformationally restricted homotryptamines

10.1021/ol050790n

The research explores a method for synthesizing conformationally restricted homotryptamine-like compounds, which are of interest in drug discovery for their potential as selective serotonin reuptake inhibitors (SSRIs). The study focuses on the catalytic asymmetric cyclopropanation of 1-tosyl-3-vinylindoles using ethyl- and tert-butyldiazoacetate, catalyzed by pybox-Ru(II) complexes. The aim is to develop a scalable and efficient synthesis that avoids the use of diazomethane and offers greater catalytic efficiency than existing methods. The researchers found that 1-tosyl-3-vinylindoles are excellent substrates for this reaction, yielding N-protected trans-2-(indol-3-yl)-1-cyclopropanecarboxylic esters with good yields and high enantiomeric excess (81?88% ee). The study demonstrates the utility of this method by converting one of the cycloadducts into the potent SSRI BMS-505130, which showed a 10-fold improvement in binding potency to the serotonin transporter compared to a more flexible analogue. The findings suggest that this catalytic asymmetric cyclopropanation method is a valuable approach for synthesizing conformationally restricted homotryptamines with potential therapeutic applications.

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