194490-14-7

Basic information

• Product Name: 5-CHLORO-3-CYANOINDOLE
• Synonyms: 5-CHLORO-3-CYANOINDOLE;5-CHLORO-1H-INDOLE-3-CARBONITRILE5-CHLORO-3-CYANOINDOLE;5-chloro -1H-indole-3-carbonitrile;1H-INDOLE-3-CARBONITRILE, 5-CHLORO-
• CAS NO: 194490-14-7
• Molecular Formula: C9H5ClN2
• Molecular Weight: 176.6
• Product Categories: pharmacetical
• Mol File: 194490-14-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 198-199 °C
• Boiling Point: 383.8 °C at 760 mmHg
• Flash Point: 185.9 °C
• Appearance: /
• Density: 1.41
• Vapor Pressure: 4.28E-06mmHg at 25°C
• Refractive Index: 1.686
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 13.69±0.30(Predicted)
• CAS DataBase Reference: 5-CHLORO-3-CYANOINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-3-CYANOINDOLE(194490-14-7)
• EPA Substance Registry System: 5-CHLORO-3-CYANOINDOLE(194490-14-7)

Safety Data

• Hazardous Substances Data: 194490-14-7(Hazardous Substances Data)

Usage

General Description

5-Chloro-3-cyanoindole is a chemical compound with the molecular formula C10H6ClN3. It is a derivative of indole, which is a heterocyclic aromatic compound commonly found in nature. 5-Chloro-3-cyanoindole is used as a precursor in the synthesis of various pharmaceuticals and agrochemicals due to its role as a building block for more complex organic molecules. It is also used in research and development as a reagent and intermediate in organic synthesis. The chloro and cyano substituents on the indole ring contribute to its unique chemical properties, making it useful for a wide range of applications in the pharmaceutical and chemical industries.

InChI:InChI=1/C9H5ClN2/c10-7-1-2-9-8(3-7)6(4-11)5-12-9/h1-3,5,12H

Upstream product

• 90271-86-6 5-bromo-1H-indole-3-carbonitrile 
• 17422-32-1 5-chloro-1H-indole 
• 140-29-4 phenylacetonitrile 
• 1261024-31-0 5-chloro-1H-indole-3-carbaldehyde oxime 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 75-05-8 acetonitrile 
• 827-01-0 5-chloro-1H-indole-3-carboxaldehyde 

Downstream Products

• 10406-05-0 5-chloro-1H-indole-3-carboxylic acid 

Relevant articles and documents

Indole cyanation via CH bond activation under catalysis of Ru(III)-exchanged NaY zeolite (RuY) as a recyclable catalyst

Selective 3-cyanation of indoles was achieved under heterogeneous catalysis of Ru(III)-exchanged NaY zeolite (RuY) as a recyclable catalyst, in combination with K4[Fe(CN)6] as a nontoxic, slow cyanide releasing agent. Under the aforementioned conditions, good yields of the desired products were obtained.

2,6-Disubstituted imidazo[2,1-b][1,3,4]thiadiazole derivatives as potent staphylococcal biofilm inhibitors

A class of 36 new 2-(6-phenylimidazo[2,-1-b][1,3,4]thiadiazol-2-yl)-1H-indoles was efficiently synthesized and evaluated for their anti-biofilm properties against the Gram-positive bacterial reference strains Staphylococcus aureus ATCC 25923, S. aureus ATCC 6538 and Staphylococcus epidermidis ATCC 12228, and the Gram-negative strains Pseudomonas aeruginosa ATCC 15442 and Escherichia coli ATCC 25922. Many of these new compounds, were able to inhibit biofilm formation of the tested staphylococcal strains showing BIC50 lower than 10 μg/ml. In particular, derivatives 9c and 9h showed remarkable anti-biofilm activity against S. aureus ATCC 25923 with BIC50 values of 0.5 and 0.8 μg/ml, respectively, whereas compound 9aa was the most potent against S. aureus ATCC 6538, with a BIC50 of 0.3 μg/ml. Remarkably, these compounds showed effects in the early stages of the biofilm formation without affecting the mature biofilm of the same strains and the viability of the planktonic form. Their ability in counteracting a virulence factor (biofilm formation) without interfering with the bacterial growth in the free life form make them novel valuable anti-virulence agents.

Copper-mediated cyanation of indoles and electron-rich arenes using DMF as a single surrogate

The copper-mediated cyanation of indoles with DMF as a single surrogate has been realized. This approach could be applied for the cyanation of some electron-rich arenes and aryl aldehydes as well. Aryl aldehydes were demonstrated to be the key intermediates in the cascade process of cyanation of indoles and electron-rich arenes.