5-CHLORO-3-CYANOINDOLE

Base Information

• Chemical Name: 5-CHLORO-3-CYANOINDOLE
• CAS No.: 194490-14-7
• Molecular Formula: C₉H₅ClN₂
• Molecular Weight: 176.605
• Hs Code.: 2933990090
• Mol file: 194490-14-7.mol

Synonyms:5-Chloro-1H-indole-3-carbonitrile;5-Chloro-3-cyanoindole;

Chemical Property of 5-CHLORO-3-CYANOINDOLE

Chemical Property:

• Vapor Pressure: 4.28E-06mmHg at 25°C
• Melting Point: 198-199 °C
• Refractive Index: 1.686
• Boiling Point: 383.8 °C at 760 mmHg
• PKA: 13.69±0.30(Predicted)
• Flash Point: 185.9 °C
• PSA: 39.58000
• Density: 1.41 g/cm³
• LogP: 2.69298
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

5-Chloro-3-cyanoindole 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-CHLORO-3-CYANOINDOLE

There total 9 articles about 5-CHLORO-3-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: 86.0%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + 5-chloro-1H-indole (17422-32-1) → 5-chloro-1H-indole-3-carbonitrile (194490-14-7)

Guidance literature:

With oxygen; ammonium carbonate; copper dichloride; In dimethyl sulfoxide; at 110 ℃; for 24h; under 760.051 Torr; Schlenk technique;

DOI:10.1039/c3cc49339c

Reference yield: 82.0%

5-chloro-1H-indole (17422-32-1) + phenylacetonitrile (140-29-4) → 5-chloro-1H-indole-3-carbonitrile (194490-14-7)

Guidance literature:

With copper(l) iodide; In N,N-dimethyl-formamide; at 100 ℃; for 34h;

DOI:10.1016/j.tet.2013.03.089

Reference yield: 76.0%

5-bromo-1H-indole-3-carbonitrile (90271-86-6) → 5-chloro-1H-indole-3-carbonitrile (194490-14-7)

Guidance literature:

With copper(l) chloride; In 1-methyl-pyrrolidin-2-one; at 205 - 210 ℃; for 15h;

DOI:10.5012/jkcs.2011.55.2.240

upstream raw materials:

5-bromo-1H-indole-3-carbonitrile

5-chloro-1H-indole

phenylacetonitrile

5-chloro-1H-indole-3-carbaldehyde oxime

Downstream raw materials:

5-chloro-1H-indole-3-carboxylic acid

Refernces

• 1、 Cascioferro, Stella,Petri, Giovanna Li,Parrino, Barbara,Carbone, Daniela,Funel, Niccola,Bergonzini, Cecilia,Mantini, Giulia,Dekker, Henk,Geerke, Daan,Peters, Godefridus J.,Cirrincione, Girolamo,Giovannetti, Elisa,Diana, Patrizia. "Imidazo[2,1-b] [1,3,4]thiadiazoles with antiproliferative activity against primary and gemcitabine-resistant pancreatic cancer cells". . . Retrieved 2020/02/03.
• 2、 Zhang, Lianpeng,Lu, Ping,Wang, Yanguang. "Erratum: Copper-mediated cyanation of indoles and electron-rich arenes using DMF as a single surrogate (Org. Biomol. Chem. (2015) 13 (8322-8329))". . p. 1840 - 1840. Retrieved 2016/02/09.