5-Cyanoindole

Base Information

• Chemical Name: 5-Cyanoindole
• CAS No.: 15861-24-2
• Molecular Formula: C9H6N2
• Molecular Weight: 142.16
• Hs Code.: 29339990
• European Community (EC) Number: 239-986-4
• DSSTox Substance ID: DTXSID40166477
• Nikkaji Number: J219.871A
• Wikipedia: 5-cyanoindole
• Wikidata: Q69756922
• ChEMBL ID: CHEMBL294926
• Mol file: 15861-24-2.mol

Synonyms:5-Cyanoindole;15861-24-2;1H-Indole-5-carbonitrile;INDOLE-5-CARBONITRILE;5-Cyano-1H-indole;5-Cyano indole;MFCD00005669;EINECS 239-986-4;CHEMBL294926;5-cyano-indole;5-Indolecarbonitrile;indol-5-carbonitrile;Indole, 5-cyano-;SCHEMBL91366;Indole-5-carbonitrile, 99%;DTXSID40166477;BCP26499;CS-M1444;STR04400;BDBM50220678;STK802138;AKOS005206715;AC-7424;CG-0514;PB25883;SB20070;NCGC00340972-01;240812-99-1;BP-10151;LS-82429;SY006206;AM20060210;FT-0627223;FT-0627224;EN300-97267;C-8840;AB01331743-02;F2158-0363;Z1203730728;A3327A31-2A0C-4860-8157-F2773DE25B9E;91201-84-2

Chemical Property of 5-Cyanoindole

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 4.51E-05mmHg at 25°C
• Melting Point: 106-108 °C(lit.)
• Refractive Index: 1.674
• Boiling Point: 350 °C at 760 mmHg
• PKA: 15.62±0.30(Predicted)
• Flash Point: 121.9 °C
• PSA: 39.58000
• Density: 1.24 g/cm³
• LogP: 2.03958
• Storage Temp.: 0-6°C
• Sensitive.: Air & Light Sensitive
• Solubility.: Chloroform, Hexane, Methanol
• Water Solubility.: Soluble in chloroform, hexane and methanol. Insoluble in water.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 142.053098200
• Heavy Atom Count: 11
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

5-Cyanoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=CN2)C=C1C#N
• Uses: ? ;Reactant for parallel synthesis of dihydroisoquinolines via silver and L-proline co-catalyzed three-component coupling reaction1? ;Reactant for chemoselective and regioselective preparation of benzoyl indoles2? ;Reactant for preparation of novel PPARα/γ dual agonists for potential treatment of metabolic syndrome and IDDM3? ;Reactant for preparation of 4,5-dihydrocyclopenta[c]quinolines by palladium-catalyzed ring-expansion reaction alkynes, using O2 as the oxidant4? ;Reactant for preparation of vinylindoles by hydroarylation of alkynes using indium bromi Inhibitor of enzyme. Reactant used for parallel synthesis of dihydroisoquinolines via silver and L-proline co-catalyzed three-component coupling reaction, preparation of novel PPARα/γ dual agonists for potential treatment of metabolic syndrome and IDDM, chemo selective and regioselective preparation of benzoyl indoles, 4,5-dihydrocyclopenta[c]quinolines by palladium-catalyzed ring-expansion reaction alkynes, using O2 as the oxidant and vinylindoles by hydroarylation of alkynes using indium bromide catalyst.

Technology Process of 5-Cyanoindole

There total 59 articles about 5-Cyanoindole 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: 99.0%

5-cyanoindole-3-carboxylic acid (174500-89-1) → 1H-indole-5-carbonitrile (15861-24-2,142396-06-3)

Guidance literature:

With potassium carbonate; In ethanol; at 140 ℃; Schlenk technique;

DOI:10.1080/00397911.2019.1703137

Reference yield: 98.0%

4-amino-3-ethynylbenzonitrile (412947-51-4) → 1H-indole-5-carbonitrile (15861-24-2,142396-06-3)

Guidance literature:

With P(p-C₆H₄F)3; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In N,N-dimethyl-formamide; at 85 ℃; for 2h;

DOI:10.1002/anie.200604183

Reference yield: 96.0%

3-methyl-4-nitrobenzonitrile (96784-54-2) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 1H-indole-5-carbonitrile (15861-24-2,142396-06-3)

Guidance literature:

3-methyl-4-nitrobenzonitrile; N,N-dimethyl-formamide dimethyl acetal; With pyrrolidine; In dichloromethane; at 50 - 55 ℃; for 8h; Large scale; Green chemistry;

With iron; acetic acid; In methanol; at 0 - 55 ℃; for 8h; Reagent/catalyst; Solvent; Temperature; Large scale; Green chemistry;

DOI:10.14233/ajchem.2020.22717

upstream raw materials:

5-cyano-1H-indole-2-carboxylic acid

5-bromo-1H-indole

copper(I) cyanide

trans-5-cyano-β-dimethylamino-2-nitrostyrene

Downstream raw materials:

1-(4-fluorophenyl)-5-cyano-1H-indole

1-benzyl-1H-indole-5-carbonitrile

1-ethyl-1H-indole-5-carbonitrile

3-formyl-1H-indole-5-carbonitrile

Refernces

• 1、 Cai, Mingzhong,Huang, Bin,Liu, Rong,Xu, Caifeng. "Recyclable and Reusable Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide". . . Retrieved 2021/12/03.
• 2、 Utsumi, Tatsuki,Noda, Kenta,Kawauchi, Daichi,Ueda, Hirofumi,Tokuyama, Hidetoshi. "Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst". supporting information. p. 3583 - 3588. Retrieved 2020/08/05.