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

Base Information

• Chemical Name: 3-(1H-indol-3-yl)-3-oxopropanenitrile
• CAS No.: 20356-45-0
• Molecular Formula: C11H8N2O
• Molecular Weight: 184.197
• Hs Code.: 2933990090
• European Community (EC) Number: 833-587-4
• DSSTox Substance ID: DTXSID90368727
• Nikkaji Number: J2.111.492H
• Wikidata: Q82155497
• ChEMBL ID: CHEMBL3233064
• Mol file: 20356-45-0.mol

Synonyms:3-(1H-indol-3-yl)-3-oxopropanenitrile;20356-45-0;3-(1H-Indol-3-yl)-3-oxo-propionitrile;3-(Cyanoacetyl)indole;3-cyanoacetylindole;MFCD04610443;3-(1H-lndol-3-yl)-3-oxo-propionitrile;1H-Indole-3-propanenitrile, beta-oxo-;1H-Indole-3-propanenitrile,b-oxo-;3-cyanoacetyl indole;3-(cyanoacetyl) indole;3-(Cyanoacetyl)-1H-indole;SCHEMBL1426369;3-(2-Cyanoacetyl)-1H-indole;CHEMBL3233064;DTXSID90368727;HMS1729D01;AMY39742;BCP24133;BBL012852;STK695688;AKOS000116510;BC-0809;2-(1H-indol-3-yl)-2-oxoethyl cyanide;NCGC00335246-01;C3197;FT-0665264;EN300-05930;AB01328036-02;A879691;J-510429;3-(1H-Indol-3-yl)-3-oxopropanenitrile, AldrichCPR;Z56928903;F2113-0204

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

Chemical Property:

• Appearance/Colour: Solid
• Vapor Pressure: 3.43E-08mmHg at 25°C
• Melting Point: 241°C
• Refractive Index: 1.663
• Boiling Point: 447.2 °C at 760 mmHg
• PKA: 8.39±0.30(Predicted)
• Flash Point: 224.3 °C
• PSA: 56.65000
• Density: 1.285 g/cm³
• LogP: 2.26428
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Dimethylformamide
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 184.063662883
• Heavy Atom Count: 14
• Complexity: 278

Purity/Quality:

97% ^*data from raw suppliers

3-Cyanoacetylindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 25-36
• Safety Statements: 26-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)C(=O)CC#N
• Uses: 3-Cyanoacetylindole (cas# 20356-45-0) is a compound useful in organic synthesis.

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

There total 4 articles about 3-(1H-indol-3-yl)-3-oxopropanenitrile 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%

indole (120-72-9) + cyanoacetic acid (372-09-8) → 3-(1H-indol-3-yl)-3-oxo-propionitrile (20356-45-0)

Guidance literature:

cyanoacetic acid; With acetic anhydride; at 85 ℃; for 0.166667h;

indole; for 0.5h; Further stages.; Heating;

DOI:10.1002/jhet.5570440119

Reference yield: 84.0%

indole (120-72-9) + potassium 2-cyanoacetate (7062-95-5) → 3-(1H-indol-3-yl)-3-oxo-propionitrile (20356-45-0)

Guidance literature:

With methyl chlorosulfate; In acetonitrile; for 1h; Ambient temperature;

Reference yield:

3-chloroacetylindole (28755-03-5) + potassium cyanide (151-50-8) → 3-(1H-indol-3-yl)-3-oxo-propionitrile (20356-45-0)

Guidance literature:

In water; benzene; at 50 ℃; for 1h;

DOI:10.1002/jhet.5570440119

upstream raw materials:

indole

potassium 2-cyanoacetate

cyanoacetic acid

3-chloroacetylindole

Downstream raw materials:

(E)-3-(1H-indol-3-yl)acrylonitrile

4-(4-bromophenyl)-2-(1H-indol-3-yl)-6-(2-thienyl)nicotinonitrile

2-(1H-indol-3-yl)-4-phenyl-6-(2-thienyl)nicotinonitrile

2-(1H-indol-3-yl)-4-(4-nitrophenyl)-6-(2-thienyl)nicotinonitrile

Refernces

Synthesis and anti-inflammatory activity of 3-indolyl pyridine derivatives through one-pot multi component reaction

10.1007/s12039-010-0070-3

The research aims to develop an efficient method for synthesizing 3-indolyl pyridine derivatives and evaluate their anti-inflammatory and analgesic activities. The study employs a one-pot multi-component reaction under reflux conditions using key chemicals such as 3-cyanoacetyl indole, various aldehydes, malononitrile, and sodium methoxide or sodium hydroxide. The synthesized compounds were characterized by IR, NMR, and mass spectroscopy. The results showed that these compounds exhibited significant anti-inflammatory activity, comparable to the standard drug indomethacin, and some bis-Hantzsch dihydropyridine derivatives demonstrated notable analgesic activity, similar to aspirin. The study concludes that the one-pot multi-component reaction is an efficient and convenient method for synthesizing these biologically active compounds, and further research is ongoing to explore the scope and limitations of this methodology.