3-(1H-indol-3-yl)propanamide

Base Information

• Chemical Name: 3-(1H-indol-3-yl)propanamide
• CAS No.: 5814-93-7
• Molecular Formula: C11H12 N2 O
• Molecular Weight: 188.229
• Hs Code.: 2933990090
• European Community (EC) Number: 855-919-7
• NSC Number: 523262
• UNII: 6RD94WRM73
• DSSTox Substance ID: DTXSID40326054
• Nikkaji Number: J3.409.614G
• Wikipedia: Indolepropionamide
• Wikidata: Q25102177
• ChEMBL ID: CHEMBL1338144
• Mol file: 5814-93-7.mol

Synonyms:3-(1H-indol-3-yl)propanamide;5814-93-7;Indole-3-propionamide;indolepropionamide;6RD94WRM73;UNII-6RD94WRM73;NSC 523262;NSC-523262;1H-Indole-3-propanamide;indole-3-propanamide;3-(3-Indole)-propionamide;3-(1H-Indol-3-yl)-propionamide;NSC523262;Cambridge id 5102096;MLS000104385;SCHEMBL664283;CHEMBL1338144;DTXSID40326054;3-(3-INDOLYL)PROPANAMIDE;HMS1679B04;HMS2288H03;CCG-20524;MFCD00152109;AKOS000520283;BS-28961;SMR000054320;AM20040773;FT-0627220;EN300-67051;I-3980;Z33546345;F0920-2312;V9X

Chemical Property of 3-(1H-indol-3-yl)propanamide

Chemical Property:

• Vapor Pressure: 1.17E-09mmHg at 25°C
• Melting Point: 169-170 °C
• Boiling Point: 487.6°Cat760mmHg
• PKA: 16.59±0.40(Predicted)
• Flash Point: 248.7°C
• PSA: 58.88000
• Density: 1.238g/cm³
• LogP: 2.28610
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 188.094963011
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

98%min ^*data from raw suppliers

Indole-3-propionamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CCC(=O)N
• Uses: Indole-3-propionamide is a novel endogenous indole derivative which has a similar structure to melatonin. It acts as a stabilizer of energy metabolism, thereby reducing reactive oxygen species (ROS) production.

Technology Process of 3-(1H-indol-3-yl)propanamide

There total 5 articles about 3-(1H-indol-3-yl)propanamide 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: 96.0%

Indole-3-propionic acid (830-96-6) → 3-(3-indolyl)-propanamide (5814-93-7)

Guidance literature:

Indole-3-propionic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; for 1.5h;

With ammonia; In tetrahydrofuran; at 20 ℃; for 2.5h;

DOI:10.1021/jm0304010

Reference yield: 96.0%

3-(1H-indol-3-yl)propanehydrazide (20401-90-5) → 3-(3-indolyl)-propanamide (5814-93-7)

Guidance literature:

nickel; In ethanol; for 2.5h; Heating / reflux;

Reference yield: 90.0%

Methyl indole-3-propionate (5548-09-4) → 3-(3-indolyl)-propanamide (5814-93-7)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 48h;

DOI:10.1135/cccc20021669

upstream raw materials:

Indole-3-propionic acid

Methyl indole-3-propionate

3-(1H-indol-3-yl)propanehydrazide

methyl chloroformate

Downstream raw materials:

Homotryptamine

Refernces

• 1、 Uyanik, Muhammet,Tanaka, Hiroki,Ishihara, Kazuaki. "Hypoiodite-Catalyzed Chemoselective Tandem Oxidation of Homotryptamines to Peroxy- And Epoxytetrahydropyridoindolenines". supporting information. p. 8049 - 8054. Retrieved 2020/11/02.
• 2、 -. "INDOLINE DERIVATIVES, COMPOSITIONS COMPRISING THEM AND USES THEREOF". Page/Page column 60. . Retrieved 2017/09/24.