115666-46-1

Basic information

• Product Name: 6-IODO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE
• Synonyms: 6-IODO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE;6-Iodoindoline;2,3-Dihydro-6-iodo-1H-indole
• CAS NO: 115666-46-1
• Molecular Formula: C₈H₈IN
• Molecular Weight: 245.06
• EINECS: 604-604-1
• Mol File: 115666-46-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 83-90 °C
• Boiling Point: 289.617 °C at 760 mmHg
• Flash Point: 128.956 °C
• Appearance: /
• Density: 1.794 g/cm³
• PKA: 4.37±0.20(Predicted)
• CAS DataBase Reference: 6-IODO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-IODO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE(115666-46-1)
• EPA Substance Registry System: 6-IODO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE(115666-46-1)

Safety Data

• Hazardous Substances Data: 115666-46-1(Hazardous Substances Data)

Usage

General Description

6-IODO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE is a chemical compound that is commonly used in the pharmaceutical industry as a building block for the synthesis of various drugs and biologically active molecules. It is a derivative of the indole ring structure and contains an iodo group, making it useful for the introduction of halogen atoms into organic molecules. Its hydrochloride salt form enhances its solubility in water and makes it easier to handle in laboratory settings. 6-IODO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE has potential applications in the development of new pharmaceuticals and agrochemicals, and is an important tool for organic chemists in the synthesis of complex molecules. However, it is important to handle this chemical with care, as it may have hazardous properties and should be used in accordance with proper safety protocols.

Upstream product

• 22949-08-2 1-acetyl-6-nitro-2,3-dihydroindole 
• 4769-96-4 6-nitroindole 
• 63839-24-7 6-bromo-indoline 
• 41252-97-5 4-iodo-2-nitrotoluene 
• 106-49-0 p-toluidine 
• 52415-29-9 6-bromo-1H-indole 
• 62368-29-0 1-acetyl-6-aminoindoline 
• 115666-43-8 1-acetyl-2,3-dihydro-6-iodoindole 
• 19727-83-4 6-nitroindoline 
• 115666-47-2 6-iodo-1 H-indole 

Downstream Products

• 954239-34-0 C₁₃H₁₆INO₂ 

Relevant articles and documents

Diastereoselective Total Synthesis of Raputindole A

The first diastereoselective total synthesis of the bisindole alkaloid raputindole A is reported. After Au(I)-catalyzed assembly of the cyclopenta[f]indole tricycle, it was possible to hydrogenate the indene double bond regio- A nd diastereoselectively through iridium catalysis, guided by a preinstalled hydroxy function. Attempted HWE reaction led to formal elimination of formaldehyde from an α-quaternary cyclopentane carbaldehyde, which was circumvented by Takai olefination. After Suzuki-Miyaura cross coupling and deprotection/oxidation, (±)-raputindole A was obtained in 13 linear steps in 18% overall yield.

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.

Synthesis of Pyranocyclopentaindolines Representing the Western Sections of Janthitrem B, JBIR-137, and Shearinine G

The synthesis of the ABCD tetracyclic partial structures of the fungal indole diterpenes janthitrem B, JBIR-137, and shearinine G is reported. The route starts from 5-formylated indoline that is coupled to a dihydropyran moiety, followed by Prins cyclization. A diene was obtained that was oxygenated in a divergent manner. The hydroxylated tetracyclic western half of janthitrem B was obtained in eight steps and 10 % overall yield. We also share our experience with alternative approaches passing via alkynylated precursors. This includes the gold-catalyzed cycloisomerization of a 6-ethynyl-5-prenylindoline.

NEAR-INFRARED NERVE-SPARING FLUOROPHORES

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