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

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

Downstream Products

• 114144-17-1 5-iodo-1H-indole-3-carbaldehyde 
• 174715-24-3 5-iodo-1-(4-methylphenylsulfonyl)indole 
• 280563-07-7 1-methyl-5-iodoindole 
• 460087-41-6 5-iodo-1-phenylsulfonyl-1H-indole 
• 889108-53-6 5-(3-benzyloxyprop-1-enyl)-1H-indole 
• 374818-68-5 5-(2-phenylethynyl)-1H-indole 
• 15861-24-2 1H-indole-5-carbonitrile 
• 114144-16-0 5-iodo-2,3-dihydro-1H-indole 
• 889108-48-9 5-ethynyl-1H-indole 
• 889108-55-8 5-(3-benzyloxypropyl)-1H-indole 
• 889108-58-1 3-(2,5-dioxopyrrolidin-3-yl)-5-(2-phenylethyl)-1H-indole 
• 889108-61-6 3-(2,5-dihydro-2,5-dioxopyrrol-3-yl)-5-(2-phenylethyl)-1H-indole 
• 889108-60-5 5-(3-benzyloxypropyl)-3-(2,5-dihydro-2,5-dioxopyrrol-3-yl)-1H-indole 
• 889108-57-0 5-(3-benzyloxypropyl)-3-(2,5-dioxopyrrolidin-3-yl)-1H-indole 

Relevant articles and documents

Copper-catalyzed conversion of aryl and heteroaryl bromides into the corresponding iodide

An efficient method for the synthesis of aryl and heteroaryl iodides is described in this study. The reactions of aryl and heteroaryl bromides with potassium iodide proceeded smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding iodides in satisfactory to excellent yields.

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.

Photo-induced Metal-Catalyst-Free Aromatic Finkelstein Reaction

The facile iodination of aromatic compounds under mild conditions is a great challenge for both organic and medicinal chemistry. Particularly, the synthesis of functionalized aryl iodides by light has long been considered impossible due to their photo-lability, which actually makes aryl iodides popular starting materials in many photo-substitution reactions. Herein, a photo-induced halogen exchange in aryl or vinyl halides has been discovered for the first time. A broad scope of aryl iodides can be prepared in high yields at room temperature under exceptionally mild conditions without any metal or photo-redox catalysts. The presence of a catalytic amount of elemental iodine could promote the reaction significantly.

Deformylation of indole and azaindole-3-carboxaldehydes using anthranilamide and solid acid heterogeneous catalyst via quinazolinone intermediate

The deformylation of indole and azaindole-3-carboxaldehydes was achieved in the presence of anthranilamide and a solid acid heterogeneous catalyst under reflux conditions in 25-90% yield. The reaction proceeds via quinazolinone intermediate, which undergoes acid catalyzed cleavage to form deformylated product.

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.

COPPER-CATALYZED FORMATION OF CARBON-HETEROATOM AND CARBON-CARBON BONDS

One aspect of the present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-sulfur bond between the sulfur atom of a thiol moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper(II)-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-carbon bond between the carbon atom of cyanide ion and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In another embodiment, the present invention relates to a copper-catalyzed method of transforming and aryl, heteroaryl, or vinyl iodide. Yet another embodiment of the present invention relates to a tandem method, which may be practiced in a single reaction vessel, wherein the first step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl iodide from the corresponding aryl, heteroaryl, or vinyl chloride or bromide; and the second step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl nitrile, amide or sulfide from the aryl, heteroaryl, or vinyl iodide formed in the first step.

Copper-catalyzed halogen exchange in aryl halides: An aromatic finkelstein reaction

A mild and general method for the conversion of aryl, heteroaryl, and vinyl bromides into the corresponding iodides was developed utilizing a catalyst system comprising 5 mol % of Cul and 10 mol % of a 1,2- or 1,3-diamine ligand. A variety of polar functional groups are tolerated, and even N-H containing substrates such as sulfonamides, amides, and indoles are compatible with the reaction conditions. Both the reaction rate and the equilibrium conversion of the aryl bromide depend on the choice of the halide salt and the solvent. The best results were obtained using Nal as the halide salt and dioxane, n-butanol, or n-pentanol as the solvents. Copyright

Cedranediolborane as a borylating agent for the preparation of boronic acids: Synthesis of a boronated nucleoside analogue

Cedranediolborane can be cross-coupled with aryl iodides under Pd(0) catalysis to yield aryl boronates which can easily be deprotected to form the corresponding free boronic acids. The application of this methodology has led to the preparation of a boronated nucleoside indole analogue.

The Chemistry of Indoles. XXXIX. A Facile Synthetic Method for 7-Substituted Indoles

A simple four-step synthetic method for 7-iodo-, 7-bromo- and 7-chloroindole was established with high overall yield starting from 2,3-dihydroindole.Several 7-substituted indoles carrying a carbon side chain and 7-methoxyindole were also synthetized.Keywords - thallation; 7-substituted indole; regioselective metalation; 7-iodoindole; 7-bromoindole; 7-chloroindole; 7-methoxyindole; methyl 3-(indol-7-yl)acrylate; 4-(indol-7-yl)-2-methyl-3-buten-2-ol; Heck reaction