23084-36-8

Basic information

• Product Name: 3-CYANO-5-METHOXYINDOLE
• Synonyms: 1H-INDOLE-3-CARBONITRILE, 5-METHOXY-;3-CYANO-5-METHOXYINDOLE;5-METHOXY-1H-INDOLE-3-CARBONITRILE
• CAS NO: 23084-36-8
• Molecular Formula: C₁₀H₈N₂O
• Molecular Weight: 172.18
• Product Categories: pharmacetical
• Mol File: 23084-36-8.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 385 °C at 760 mmHg
• Flash Point: 186.6 °C
• Appearance: /
• Density: 1.26 g/cm³
• Vapor Pressure: 3.94E-06mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: 2-8°C
• PKA: 14.31±0.30(Predicted)
• CAS DataBase Reference: 3-CYANO-5-METHOXYINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYANO-5-METHOXYINDOLE(23084-36-8)
• EPA Substance Registry System: 3-CYANO-5-METHOXYINDOLE(23084-36-8)

Safety Data

• Hazardous Substances Data: 23084-36-8(Hazardous Substances Data)

Usage

General Description

3-Cyano-5-methoxyindole is a chemical compound with the molecular formula C11H9NO. It is a derivative of indole, containing a cyano group (-CN) and a methoxy group (-OCH3) at the 3 and 5 positions, respectively. 3-CYANO-5-METHOXYINDOLE is commonly used in organic synthesis and pharmaceutical research as a building block for the production of various biologically active molecules and pharmaceutical drugs. It is known for its potential antitumor, anti-inflammatory, and antimicrobial properties, and has been the subject of several research studies for its pharmacological and therapeutic potential. Additionally, 3-cyano-5-methoxyindole has been reported to exhibit fluorescent properties and is used as a fluorescent labeling reagent in biological and chemical assays.

InChI:InChI=1/C10H8N2O/c1-13-8-2-3-10-9(4-8)7(5-11)6-12-10/h2-4,6,12H,1H3

Upstream product

• 10601-19-1 5-methoxyindole-3-carboxaldehyde 
• 1006-94-6 5-methoxylindole 
• 7440-44-0 pyrographite 
• 73930-99-1 1-nitro-2-(prop-1-en-1-yl)benzene 
• 140-29-4 phenylacetonitrile 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 75-52-5 nitromethane 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 135205-66-2 N?cyanosuccinimide 
• 75-05-8 acetonitrile 
• 928664-98-6 4-isoxazoleboronic acid pinacol ester 

Downstream Products

• 60523-82-2 5-methoxy-3-aminomethyl indole 
• 1338059-36-1 C₃₄H₂₆Cl₂N₄O₂S 

Relevant articles and documents

Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions

Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.

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.

3-(6-phenylimidazo [2,1-b][1,3,4]thiadiazol-2-yl)-1HIndole derivatives as new anticancer agents in the treatment of pancreatic ductal adenocarcinoma

A new series of imidazo[2,1-b][1,3,4]thiadiazole derivatives was efficiently synthesized and screened for their in vitro antiproliferative activity on a panel of pancreatic ductal adenocarcinoma (PDAC) cells, including SUIT-2, Capan-1 and Panc-1. Compounds 9c and 9l, showed relevant in vitro antiproliferative activity on all three pre-clinical models with half maximal inhibitory concentration (IC50) ranging from 5.11 to 10.8 μM, while the compounds 9e and 9n were active in at least one cell line. In addition, compound 9c significantly inhibited the migration rate of SUIT-2 and Capan-1 cells in the scratch wound-healing assay. In conclusion, our results will support further studies to increase the library of imidazo [2,1-b][1,3,4] thiadiazole derivatives for deeper understanding of the relationship between biological activity of the compounds and their structures in the development of new antitumor compounds against pancreatic diseases.