16066-91-4

Basic information

• Product Name: 5-IODOINDOLE
• Synonyms: 5-IODO-1H-INDOLE;5-IODOINDOLE;5-Indoindole;5-Iodo-1H-indole, 95+%;5-Iodoindole 97%;5-Iodo-1H-indole 97%;5-Iodo-1H-indole97%
• CAS NO: 16066-91-4
• Molecular Formula: C₈H₆IN
• Molecular Weight: 243.04
• Product Categories: blocks;IndolesOxindoles;Iodides;Indoles and derivatives;Halides;Pyrroles & Indoles;Halogenated Heterocycles;Heterocyclic Building Blocks;Indoles;IndolesBuilding Blocks
• Mol File: 16066-91-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 101-104 °C(lit.)
• Boiling Point: 341.705 °C at 760 mmHg
• Flash Point: 160.458 °C
• Appearance: White to pale brown/Solid or Crystalline Solid
• Density: 1.961 g/cm³
• Vapor Pressure: 0.000156mmHg at 25°C
• Refractive Index: 1.768
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 16.14±0.30(Predicted)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 5-IODOINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-IODOINDOLE(16066-91-4)
• EPA Substance Registry System: 5-IODOINDOLE(16066-91-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37
• WGK Germany: 3
• Hazardous Substances Data: 16066-91-4(Hazardous Substances Data)

Usage

Uses

5-Iodoindole is an important organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field. It is used as the starting material in the synthesis of 5-(α-fluorovinyl)-N-tosylindole.

General Description

5-Iodoindole can be synthesized via nitration of m-toluidine.

InChI:InChI=1/C8H6IN/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,10H

Upstream product

• 99066-64-5 5-iodo-1H-indole-2-carboxylic acid 
• 114144-16-0 5-iodo-2,3-dihydro-1H-indole 
• 10075-50-0 5-bromo-1H-indole 
• 114144-17-1 5-iodo-1H-indole-3-carbaldehyde 
• 99066-66-7 (5-iodo-2-nitro-phenyl)-pyruvic acid 
• 61995-51-5 1-acetyl-2,3-dihydro-5-iodoindole 
• 331432-91-8 5-bromo-1-(tert-butyldimethylsilyl)-1H-indole 
• 331432-92-9 1-(tert-butyldimethylsilyl)-5-iodo-1H-indole 

Downstream Products

• 174715-24-3 5-iodo-1-(4-methylphenylsulfonyl)indole 
• 280563-07-7 1-methyl-5-iodoindole 
• 889108-53-6 5-(3-benzyloxyprop-1-enyl)-1H-indole 
• 374818-68-5 5-(2-phenylethynyl)-1H-indole 
• 114144-16-0 5-iodo-2,3-dihydro-1H-indole 
• 677702-22-6 5-iodo-1H-indazole-3-carboxaldehyde 
• 193354-13-1 5-iodo-1,3-dihydro-indol-2-one 
• 1063992-91-5 1-(4-difluoromethoxybenzenesulfonyl)-5-iodo-1H-indole 
• 1087349-08-3 1-(2-(1H-indol-5-yl)phenyl)ethanone 
• 1189117-58-5 5,5'-diiodo-3,3'-diindolyl(3,5-difluorophenyl)methane 
• 1189117-57-4 5,5'-diiodo-3,3'-diindolyl(4-methylphenyl)methane 
• 1248591-00-5 N-(3,4-dimethoxyphenethyl)-N-methyl-1H-indol-5-amine 
• 1287714-69-5 4-bromo-2-(5-iodo-1H-indol-3-ylmethyl)phenol 
• 179626-79-0 (E)-3-(1H-indol-5-yl)acrylic acid 

Relevant articles and documents

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Rapid and efficient copper-catalyzed finkelstein reaction of (hetero)aromatics under continuous-flow conditions

A general, rapid, and efficient method for the copper-catalyzed Finkelstein reaction of (hetero)aromatics has been developed using continuous flow to generate a variety of aryl iodides. The described method can tolerate a broad spectrum of functional groups, including N-H and O-H groups. Additionally, in lieu of isolation, the aryl iodide solutions were used in two distinct multistep continuous-flow processes (amidation and Mg-I exchange/nucleophilic addition) to demonstrate the flexibility of this method.

Nickel-catalysed aromatic Finkelstein reaction of aryl and heteroaryl bromides

A fast and efficient nickel-catalysed iodination reaction of aryl and heteroaryl bromides has been developed. The transformation was found to be general for a wide range of substrates and was used for the synthesis of iodo-PK11195, an imaging agent of Alzheimer's disease and iniparib, a compound used in the treatment of breast cancer.