194490-14-7

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloro-3-cyanoindole is used as a precursor in the synthesis of various pharmaceuticals for its role as a building block for more complex organic molecules. Its unique chemical properties contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
5-Chloro-3-cyanoindole is utilized as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides, due to its ability to form complex organic molecules with potential applications in agriculture for pest control and crop protection.
Used in Research and Development:
5-Chloro-3-cyanoindole serves as a reagent and intermediate in organic synthesis, facilitating the development of new chemical compounds and materials. Its unique properties make it a valuable tool in the exploration of novel chemical reactions and the synthesis of advanced organic molecules for various applications.

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Imidazo[2,1-b] [1,3,4]thiadiazoles with antiproliferative activity against primary and gemcitabine-resistant pancreatic cancer cells

A new series of eighteen imidazo [2,1-b] [1,3,4]thiadiazole derivatives was efficiently synthesized and screened for antiproliferative activity against the National Cancer Institute (NCI-60) cell lines panel. Two out of eighteen derivatives, compounds 12a and 12h, showed remarkably cytotoxic activity with the half maximal inhibitory concentration values (IC50) ranging from 0.23 to 11.4 μM, and 0.29–12.2 μM, respectively. However, two additional compounds, 12b and 13g, displayed remarkable in vitro antiproliferative activity against pancreatic ductal adenocarcinoma (PDAC) cell lines, including immortalized (SUIT-2, Capan-1, Panc-1), primary (PDAC-3) and gemcitabine-resistant (Panc-1R), eliciting IC50 values ranging from micromolar to sub-micromolar level, associated with significant reduction of cell-migration and spheroid shrinkage. These remarkable results might be explained by modulation of key regulators of epithelial-to-mesenchymal transition (EMT), including E-cadherin and vimentin, and inhibition of metalloproteinase-2/-9. High-throughput arrays revealed a significant inhibition of the phosphorylation of 45 tyrosine kinases substrates, whose visualization on Cytoscape highlighted PTK2/FAK as an important hub. Inhibition of phosphorylation of PTK2/FAK was validated as one of the possible mechanisms of action, using a specific ELISA. In conclusion, novel imidazothiadiazoles show potent antiproliferative activity, mediated by modulation of EMT and PTK2/FAK.

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.

Erratum: Copper-mediated cyanation of indoles and electron-rich arenes using DMF as a single surrogate (Org. Biomol. Chem. (2015) 13 (8322-8329))

Correction for 'Copper-mediated cyanation of indoles and electron-rich arenes using DMF as a single surrogate' by Lianpeng Zhang et al., Org. Biomol. Chem., 2015, 13, 8322-8329.

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.

Copper-mediated C3-cyanation of indoles by the combination of amine and ammonium

A copper-promoted C3-cyanation of both the free N-H and N-protected indoles by N,N,N′,N′-tetramethyl-ethane-1,2-diamine (TMEDA) and ammonium is achieved. The iminium ion acts as the intermediate in this transformation, which is sequentially electrophilically attacked by indole and H2O followed by hydrolyzation to form the aldehyde. Then the reaction between the aldehyde and ammonium afforded nitriles. The reaction employs O2 as a clean oxidant with good efficiency and functional group tolerance. Thus, it represents a facile and safe procedure leading to 3-cyano indoles. The Royal Society of Chemistry 2014.

An investigation into the substituent effect of halogen atoms on the crystal structures of indole-3-carboxylic acid (ICA)

An investigation into the substituent effect of halogen atoms (F, Cl, Br) on the crystal structure of indole-3-carboxylic acid (ICA) was prepared in this work. The investigation was done through the aspect of crystal structure, intermolecular interactions and π...π stacking motifs with the assistance of infrared spectra, elemental analyses, NMR spectra, differential scanning calorimetry (DSC), thermogravimetric analyses (TGA) and hot stage microscopy (HSM) measurements. The results revealed that the different kinds of halogen atoms and the different substituted positions have a significant effect on the crystal structures, molecular π...π stacking motifs and the kinds of intermolecular interactions. We further correlated the melting points of the ICAs with the H-H, O-H and X-H (X = F, Cl, Br) interactions, and found a positive correlation between them.

Cyanation of indoles with benzyl cyanide as the cyanide anion surrogate

A copper-mediated direct cyanation of indoles with benzyl cyanide as the cyanide anion surrogate has been achieved. The cascade reaction furnished 3-cyanoindoles under mild reaction conditions in good to excellent yields with various functional groups tolerance.

Highly convenient and large scale synthesis of 5-chloroindole and its 3-substituted analogues

A large scale and commercially feasible synthesis of 5-chloroindole and its 3-substituted analogues has been described via a halogen - halogen exchange reaction from 5-bromoindole and its derivatives using cuprous chloride and dipolar aprotic solvent N-methyl-2-pyrrolidone in one pot with good yields.

Synthesis and characterization of homo binuclear complexes of UO 2(VI), Th(IV), zro(IV) and VO(IV) with polyaza macrocyclic schiff-bases

The synthesis and characterization of homo binuclear complexes with some Schiff base monohydrazone derivatives obtained from the reaction of thiocarbohydrazide, benzilmonohydrazone/diacetylmonohydrazone and acetylacetone in presence of UO22+, ZrO2+, Th4+ and VO2+ ions were reported. An ethanolic solution of hydrated UO2(VI)/Th(IV)/ZrO(IV) nitrates/vanadyl sulphate was added to a hot ethanolic solution of the mixture of thiocarbohydrazide. The resulting mixture was refluxed on a water bath for 2-3 hours during which a coloured complex was precipitated out in each case. The ethanolic suspension of the above complexes were treated with acetylacetone and thiocarbohydrazide followed by the addition of corresponding metal salt. The results show that the complexes are highly colored and insoluble in water and common organic solvents such as ethanol, methanol, acetone, CCl4, CHCl3, benzene and ether but moderately soluble in highly coordinating solvents such as DMF and DMSO.