128200-45-3

Basic information

• Product Name: 1-ETHYL-1H-INDOLE-3-CARBONITRILE
• Synonyms: 1-ETHYL-1H-INDOLE-3-CARBONITRILE;OTAVA-BB 7020690196;1-ethyl-1H-indole-3-carbonitrile(SALTDATA: FREE);1-ethyl-3-indolecarbonitrile;1-ethylindole-3-carbonitrile;A3235/0137385;ZINC00107578
• CAS NO: 128200-45-3
• Molecular Formula: C11H10N2
• Molecular Weight: 170.22
• Mol File: 128200-45-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 335.8°C at 760 mmHg
• Flash Point: 156.9°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 0.000117mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: 1-ETHYL-1H-INDOLE-3-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ETHYL-1H-INDOLE-3-CARBONITRILE(128200-45-3)
• EPA Substance Registry System: 1-ETHYL-1H-INDOLE-3-CARBONITRILE(128200-45-3)

Safety Data

• Hazardous Substances Data: 128200-45-3(Hazardous Substances Data)

Usage

General Description

1-Ethyl-1H-indole-3-carbonitrile is a chemical compound with the molecular formula C11H10N2. It is a nitrile derivative of indole, with an ethyl group attached to the nitrogen atom. 1-ETHYL-1H-INDOLE-3-CARBONITRILE is commonly used as a building block in the synthesis of pharmaceuticals and other organic compounds. It has potential applications in the development of new drugs and biochemical research due to its ability to interact with biological targets. 1-Ethyl-1H-indole-3-carbonitrile is also used as an intermediate in the production of other chemicals, and its properties make it useful in organic synthesis and medicinal chemistry.

InChI:InChI=1/C11H10N2/c1-2-13-8-9(7-12)10-5-3-4-6-11(10)13/h3-6,8H,2H2,1H3

Upstream product

• 10604-59-8 N-Ethylindole 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 68-12-2 N,N-dimethyl-formamide 
• 58494-59-0 N-ethyl-3-formylindole 
• 250355-38-5 3-formyl-1-(2-iodoethyl)indole 
• 134785-54-9 1-(2-chloroethyl)-1H-indole-3-carbaldehyde 
• 487-89-8 Indole-3-carboxaldehyde 
• 201230-82-2 carbon monoxide 
• 250355-41-0 1-(2-iodoethyl)-1H-indole-3-carbonitrile 

Relevant articles and documents

An insight on the influence of surface Lewis acid sites for regioselective C–H bond C3-cyanation of indole using NH4I and DMF as combined cyanide source over Cu/SBA-15 catalyst

The Cu dispersed on mesoporous SBA-15 has demonstrated the regioselective C–H bond C3-cyanation of indoles by in-situ generation of –CN using DMF and NH4I in presence of O2. Pyridine adsorbed diffuse reflectance infrared spectroscopy (DRIFTS) results revealed that surface Cu2+ species are acting as Lewis acid sites in the in-situ generation of cyano- group for the synthesis of indole nitriles. A direct correlation between Cu metal surface area and the indole nitrile yields are established and the dual role of copper is substantiated by N2O titration and XPS techniques. The 10 wt%Cu/SBA-15 demonstrated superior performance when compared to Pd, Ru supported on SBA-15. The 10 wt%Cu/SBA-15 catalyst showed consistent activity and selectivity after the 4th cycle.

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.