224434-83-7

Basic information

• Product Name: 6-Bromo-3-cyanoindole
• Synonyms: 6-Bromo-3-cyanoindole;1H-Indole-3-carbonitrile, 6-bromo-;6-broMoindole-3-carbonitrile;6-BROMO-3-CYANO-1H-INDOLE
• CAS NO: 224434-83-7
• Molecular Formula: C₉H₅BrN₂
• Molecular Weight: 221.05
• Product Categories: Indole;Organohalides
• Mol File: 224434-83-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 405.939 °C at 760 mmHg
• Flash Point: 199.305 °C
• Appearance: /
• Density: 1.74 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.68±0.30(Predicted)
• CAS DataBase Reference: 6-Bromo-3-cyanoindole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-3-cyanoindole(224434-83-7)
• EPA Substance Registry System: 6-Bromo-3-cyanoindole(224434-83-7)

Safety Data

• Hazardous Substances Data: 224434-83-7(Hazardous Substances Data)

Usage

General Description

6-Bromo-3-cyanoindole is a chemical compound with the molecular formula C9H6BrN3. It is a derivative of indole, a bicyclic heterocyclic organic compound, and is characterized by the presence of a bromine atom and a cyano group. 6-Bromo-3-cyanoindole is often used as a building block in the synthesis of various pharmaceuticals and agrochemicals due to its versatile reactivity and structural motif. It has been studied for its potential medicinal properties, including its role as a kinase inhibitor and its anti-inflammatory effects. Additionally, 6-Bromo-3-cyanoindole is also utilized in the field of material science for the development of novel organic materials and polymers. Overall, this chemical compound has drawn significant interest in various research and industrial applications.

Upstream product

• 5457-28-3 3-cyano-1H-indole 
• 928664-98-6 4-isoxazoleboronic acid pinacol ester 
• 52415-29-9 6-bromo-1H-indole 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 1261025-00-6 C₉H₇BrN₂O 
• 17826-04-9 6-bromo-1H-indole-3-carbaldehyde 

Downstream Products

• 134029-44-0 nortopsentine B 
• 134029-43-9 nortopsentin A 

Relevant articles and documents

Efficient construction of diverse 3-cyanoindoles under novel tandem catalysis

A novel and rapid construction of 3-cyanoindoles by palladium-catalyzed tandem reactions has been developed. "N-H"free unprotected, N-alkyl and N-aryl 3-cyanoindoles are obtained with good to excellent yields. The usefulness of this synthetic approach is further demonstrated by the successful synthesis of practical compounds such as the therapeutic estrogen receptor ligand A precursor. Mechanism study shows that the tandem catalysis exploits a Suzuki cross-coupling with subsequent base-induced isoxazole fragmentation, followed by the aldimine condensation.

Marine-Natural-Product Development: First Discovery of Nortopsentin Alkaloids as Novel Antiviral, Anti-phytopathogenic-Fungus, and Insecticidal Agents

Nortopsentin alkaloids were found to have potent antiviral, anti-phytopathogenic-fungus, and insecticidal activities for the first time. Antiviral-activity tests revealed that these compounds were very sensitive to substituents, so a series of nortopsentin derivatives were designed, synthesized, and systematically evaluated for their antiviral activities against TMV, their fungicidal activities, and their insecticidal activities on the basis of a structural-diversity-derivation strategy. Compounds 2e (in vivo inactivation-, curative-, and protective-activity inhibitory rates of 50, 59, and 56%, respectively, at 500 μg/mL) and 2k (in vivo inactivation-, curative-, and protective-activity inhibitory rates of 60, 58, and 52%, respectively, at 500 μg/mL), with excellent antiviral activities and good physicochemical properties, emerged as new lead compounds for novel-antiviral-agent development. Further fungicidal-activity tests revealed that these alkaloids displayed broad-spectrum fungicidal activities. Compounds 2f, 2h, and 2j emerged as new lead compounds for antifungal-activity research. Additionally, all the compounds displayed good insecticidal activities against five kinds of insects, including Mythimna separate, Helicoverpa armigera, Ostrinia nubilalis, Plutella xylostella, and Culex pipiens pallens.

Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4- thiadiazoles

A series of 3,5-bis(indolyl)-1,2,4-thiadiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-thiocarboxamide 3 with iodobenzene diacetate underwent oxidative dimerization to give 3,5-bis(indolyl)-1,2,4-thiadiazoles 4a-n. Among the synthesized bis(indoly)-1,2,4-thiadiazoles, the compound 4h with 4-chlorobenzyl and methoxy substituents showed the most potent activity.