26340-49-8

Basic information

• Product Name: 2-IODO-1H-INDOLE
• Synonyms: 2-IODO-1H-INDOLE;1H-Indole,2-iodo-
• CAS NO: 26340-49-8
• Molecular Formula: C₈H₆IN
• Molecular Weight: 243.04
• Mol File: 26340-49-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 79-81 °C
• Boiling Point: 341.7±15.0 °C(Predicted)
• Appearance: /
• Density: 1.960±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 15.57±0.30(Predicted)
• CAS DataBase Reference: 2-IODO-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-IODO-1H-INDOLE(26340-49-8)
• EPA Substance Registry System: 2-IODO-1H-INDOLE(26340-49-8)

Safety Data

• Hazardous Substances Data: 26340-49-8(Hazardous Substances Data)

Usage

Description

2-IODO-1H-INDOLE, also known as 2-Iodoindole, is an organic compound that serves as a key intermediate in the synthesis of various biologically active molecules. It possesses a unique structure with an indole ring and an iodine atom, which contributes to its reactivity and potential applications in medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
2-IODO-1H-INDOLE is used as a synthetic intermediate for the production of arylthioindole molecules, which are a class of tubulin polymerization inhibitors. These inhibitors have potential applications in the development of anticancer drugs, as they can disrupt the normal function of tubulin, a key component of the cellular cytoskeleton, leading to the inhibition of cell division and growth.
Additionally, 2-IODO-1H-INDOLE is used as a synthetic intermediate in the synthesis of combretastatin A-4 derivatives. Combretastatin A-4 is a naturally occurring compound with anti-cancer properties, and its derivatives have been studied for their potential use in cancer therapy. The unique structure of 2-IODO-1H-INDOLE allows for the efficient synthesis of these derivatives, contributing to the development of novel cancer treatments.

Upstream product

• 476004-81-6 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 
• 87954-27-6 1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indole 
• 40899-71-6 1-benzenesulfonylindole 
• 120-72-9 indole 
• 1477-50-5 Indole-2-carboxylic acid 
• 75400-67-8 indole-1-carboxylic acid tert-butyl ester 
• 99275-44-2 2-iodo-1-(phenylsulfonyl)-1H-indole 
• 99275-45-3 2-iodo-1-<<2-(trimethylsilyl)ethoxy>methyl>indole 

Downstream Products

• 99275-44-2 2-iodo-1-(phenylsulfonyl)-1H-indole 
• 75833-63-5 2-iodo-1-methyl-1H-indole 
• 199450-21-0 1-benzyl-2-(indol-2'-yl)indole 
• 95-20-5 2-methyl-1H-indole 
• 875-79-6 1,2-dimethylindole 
• 3770-50-1 2-carbethoxyindole 
• 1477-50-5 Indole-2-carboxylic acid 
• 62048-32-2 N-methyl-N-phenyl-1H-indole-2-carboxamide 
• 17954-05-1 N-phenyl-1H-indole-2-carboxamide 
• 40899-98-7 1-benzenesulfonyl-1H,1'H-[2,2']biindolyl 
• 199450-15-2 1-benzyl-2-iodo-1H-indole 

Relevant articles and documents

Generation and reactions of 2,3-dilithio-N-methylindole. Synthesis of 2,3-disubstituted indoles

Generation of 2,3-dilithio-N-methylindole (7) from 2,3-diiodo-N-methylindole (6) and subsequent reaction with various electrophiles (NH4Cl, DMF, ClCO2Me, CO2, phthalic anhydride) affords the corresponding 2,3-disubstituted indoles in good to excellent yields (41-99%).

Aerobic Oxidative C-H Azolation of Indoles and One-Pot Synthesis of Azolyl Thioindoles by Flavin-Iodine-Coupled Organocatalysis

The aerobic oxidative cross-coupling of indoles with azoles driven by flavin-iodine-coupled organocatalysis has been developed for the green synthesis of 2-(azol-1-yl)indoles. The coupled organocatalytic system enabled the one-pot three-component synthesis of 2-azolyl-3-thioindoles from indoles, azoles, and thiols in an atom-economical manner by utilizing molecular oxygen as the only sacrificial reagent.

Heat Versus Basic Conditions: Intramolecular Dehydro-Diels-Alder Reaction of 1-Indolyl-1,6-heptadiynes for the Selective Synthesis of Substituted Carbazoles

The intramolecular dehydro-Diels-Alder reaction of 1-indolyl-1,6-heptadiynes proceeds smoothly under rather mild heating conditions to give substituted carbazoles in moderate to good yields. The reaction of 7-aryl-1-indolyl-1,6-heptadiynes under heating gives the corresponding carbazoles chemoselectively in high yields, whereas the reaction under basic conditions gives naphthalenes as major products.

Sterically controlled iodination of arenes via iridium-catalyzed C-H borylation

A mild method to prepare aryl and heteroaryl iodides by sequential C-H borylation and iodination is reported. The regioselectivity of this process is controlled by steric effects on the C-H borylation step and is complementary to existing methods to form aryl iodides. The iodination of boronic esters has potential for the synthesis of radiolabeled aryl iodides, as demonstrated by the concise synthesis of a potential tracer for SPECT imaging.