115666-47-2

Basic information

• Product Name: 6-IODOINDOLE
• Synonyms: 6-IODOINDOLE;6-Iodo-1H-indole
• CAS NO: 115666-47-2
• Molecular Formula: C₈H₆IN
• Molecular Weight: 243.05
• Mol File: 115666-47-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: 111.0-111.5℃
• Boiling Point: 341.705 °C at 760 mmHg
• Flash Point: 160.458 °C
• Appearance: /
• Density: 1.961g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.769
• Storage Temp.: 2-8°C(protect from light)
• PKA: 16.20±0.30(Predicted)
• CAS DataBase Reference: 6-IODOINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-IODOINDOLE(115666-47-2)
• EPA Substance Registry System: 6-IODOINDOLE(115666-47-2)

Safety Data

• Hazardous Substances Data: 115666-47-2(Hazardous Substances Data)

Usage

Description

6-Iodoindole is an organic compound with the molecular formula C8H6IN. It is characterized by the presence of an indole ring, which is a bicyclic structure consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. The "6-Iodo" part of its name indicates that there is an iodine atom attached to the sixth position of the indole ring. 6-Iodoindole is known for its potential applications in various fields due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
6-Iodoindole is used as a chemical intermediate for the synthesis of linear tripeptides, which are essential components in the preparation of right-hand segments of complestatin. Complestatin is a potent anti-inflammatory and anti-fibrotic agent that has shown promise in the treatment of various diseases, including cancer and idiopathic pulmonary fibrosis. The use of 6-Iodoindole in the synthesis of these tripeptides allows for the development of more effective and targeted therapies in the pharmaceutical industry.

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

Upstream product

• 62368-29-0 1-acetyl-6-aminoindoline 
• 19727-83-4 6-nitroindoline 
• 41252-97-5 4-iodo-2-nitrotoluene 
• 68-12-2 N,N-dimethyl-formamide 
• 106-49-0 p-toluidine 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 52415-29-9 6-bromo-1H-indole 
• 115666-43-8 1-acetyl-2,3-dihydro-6-iodoindole 
• 22949-08-2 1-acetyl-6-nitro-2,3-dihydroindole 
• 115666-46-1 6-iodo-2,3-dihydro-1H-indole 

Downstream Products

• 872876-52-3 (R)-N-carbobenzyloxy-6'-iodotryptophan 
• 872877-29-7 (S)-N-carbobenzyloxy-6'-iodotryptophan 
• 872876-93-2 (R)-N-carbobenzyloxy-6'-iodotryptophan tert-butyl ester 
• 872877-20-8 (R)-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-N-carbobenzyloxytryptophan 
• 872877-18-4 (R)-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-N-carbobenzyloxy-6'-iodotryptophan tert-butyl ester 
• 872876-83-0 (R,R)-(6'-iodo-N-carbobenzyloxytryptophyl)-3',5'-dichloro-4'-hydroxyphenylglycine tert-butyl ester 
• 872876-95-4 (R,R)-3-{6-[3-(N-tert-butoxycarbonyl-2-methoxycarbonylmethylamino)-5-iodo-6-methoxyphenyl]indol-3-yl}-2-carbobenzyloxyaminopropionic acid tert-butyl ester 
• 1429922-13-3 ethyl 5-(6-iodoindolin-1-yl)pentanoate 
• 1429922-27-9 C₂₈H₃₀N₈O₃ 
• 1429922-28-0 C₂₈H₃₀N₈O₃ 
• 1429922-29-1 C₃₁H₃₅N₅O₅ 
• 1429922-30-4 C₃₁H₃₅N₅O₅ 

Relevant articles and documents

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.

Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization

The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and experimental results of the biotransformation. This methodology represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.

Total Synthesis and Absolute Configuration of Raputindole A

The first total synthesis of the bisindole alkaloid raputindole A from the rutaceous plant Raputia simulans is reported. The key step is a Au(I)-catalyzed cyclization that assembles the cyclopenta[f]indole tricycle from a 6-alkynylated indoline precursor. The isobutenyl side chain was installed by Suzuki-Miyaura cross-coupling, followed by a regioselective reduction employing LiDBB. Starting from 6-iodoindole, the sequence needs nine steps and provided (±)-raputindole A in 6.6% overall yield. The absolute configuration of the natural product (+)-raputindole A was determined by quantum chemical calculation of the ECD spectrum.

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