90271-86-6

Basic information

• Product Name: 5-Bromo-3-cyanoindole
• Synonyms: 5-BROMO-3-CYANOINDOLE;5-BROMO-3-FLUOROINDOLE;5-Bromo-1H-indole-3-carbonitrile;5-BroMoindole-3-lindoleforMonitrile;1H-Indole-3-carbonitrile, 5-bromo-;5-Bromo-3-cyano-1H-indole
• CAS NO: 90271-86-6
• Molecular Formula: C₉H₅BrN₂
• Molecular Weight: 221.05
• Product Categories: pharmacetical;Indole;Organohalides
• Mol File: 90271-86-6.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 405.9 °C at 760 mmHg
• Flash Point: 199.3 °C
• Appearance: /
• Density: 1.74 g/cm³
• Vapor Pressure: 8.44E-07mmHg at 25°C
• Refractive Index: 1.726
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 13?+-.0.30(Predicted)
• CAS DataBase Reference: 5-Bromo-3-cyanoindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-3-cyanoindole(90271-86-6)
• EPA Substance Registry System: 5-Bromo-3-cyanoindole(90271-86-6)

Safety Data

• Hazardous Substances Data: 90271-86-6(Hazardous Substances Data)

Usage

General Description

5-Bromo-3-cyanoindole is a chemical compound with the molecular formula C9H5BrN2. It is a derivative of indole and belongs to the class of organic compounds known as tryptamines. 5-Bromo-3-cyanoindole is a brominated cyanated derivative of indole, and it is commonly used as a building block in the synthesis of various pharmaceutical and biologically active compounds. Its structure features a 5-bromoindole core with a cyano group attached to the third carbon position. 5-Bromo-3-cyanoindole has also been studied for its potential applications in the fields of drug discovery and medicinal chemistry.

InChI:InChI=1/C9H5BrN2/c10-7-1-2-9-8(3-7)6(4-11)5-12-9/h1-3,5,12H

Upstream product

• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 10075-50-0 5-bromo-1H-indole 
• 928664-98-6 4-isoxazoleboronic acid pinacol ester 
• 75-05-8 acetonitrile 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 75-52-5 nitromethane 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 5457-28-3 3-cyano-1H-indole 

Downstream Products

• 194490-14-7 5-chloro-1H-indole-3-carbonitrile 
• 1219741-43-1 5-bromo-1-methyl-1H-indole-3-carbonitrile 
• 1071973-78-8 5-phenyl-1H-indole-3-carbonitrile 

Relevant articles and documents

Conformationally restricted homotryptamines. Part 6: Indole-5-cycloalkyl methylamines as selective serotonin reuptake inhibitors

Racemic 5-(trans-2-aminomethylcyclopropyl)indoles, 5-(trans-2- aminomethylcyclopentyl) indoles, and 5-(cis-2-aminomethylcyclopentyl)indoles were synthesized and evaluated as selective serotonin reuptake inhibitors. These analogs followed SAR trends similar to those previously reported for 3-cycloalkyl substituted indoles. The most potent analogs exhibited single digit nanomolar inhibition at the human serotonin transporter but were 10-fold less active than the previously reported compounds.

Chemoselective Cu-catalyzed synthesis of diverseN-arylindole carboxamides, β-oxo amides andN-arylindole-3-carbonitriles using diaryliodonium salts

Chemoselective copper-catalyzed synthesis of diverseN-arylindole-3-carboxamides, β-oxo amides andN-arylindole-3-carbonitriles from readily accessible indole-3-carbonitriles, α-cyano ketones and diaryliodonium salts has been developed. DiverseN-arylindole-3-carboxamides and β-oxo amides were successfully achieved in high yields under copper-catalyzed neutral reaction conditions, and the addition of an organic base (DIPEA) resulted in a completely different selectivity pattern to produceN-arylindole-3-carbonitriles. Moreover, the importance of the developed methodology was realized by the synthesis of indoloquinolones andN-((1H-indol-3-yl)methyl)aniline and by a single-step gram-scale synthesis of the naturally occurring cephalandole A analogue.

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.