23659-87-2

Basic information

• Product Name: 4,6-DIMETHOXYINDOLE
• Synonyms: AKOS JY2083231;4,6-DIMETHOXY-1H-INDOLE;4,6-DIMETHOXYINDOLE;1H-Indole, 4,6-diMethoxy-
• CAS NO: 23659-87-2
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• Product Categories: Indoles and derivatives;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 23659-87-2.mol

Chemical Properties

• Melting Point: 122-124 °C
• Boiling Point: 343.8 °C at 760 mmHg
• Flash Point: 125.7 °C
• Appearance: /
• Density: 1.182 g/cm³
• Vapor Pressure: 0.000137mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 17.45±0.30(Predicted)
• CAS DataBase Reference: 4,6-DIMETHOXYINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-DIMETHOXYINDOLE(23659-87-2)
• EPA Substance Registry System: 4,6-DIMETHOXYINDOLE(23659-87-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 23659-87-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4,6-Dimethoxyindole is used as a reactant for the preparation of methoxy-substituted (benzyl)indolebutenoic acids, which exhibit HIV-1 integrase strand-transfer inhibition. This makes it a valuable compound in the development of antiretroviral drugs for the treatment of HIV/AIDS.
Used in Antimitotic Applications:
4,6-Dimethoxyindole is used as a reactant for the preparation of benzyl trimethoxyindoles, which serve as antimitotic agents. These compounds can disrupt cell division, making them potential candidates for the development of anticancer drugs.
Used in Antibacterial Applications:
4,6-Dimethoxyindole is used as a reactant for the preparation of antibacterial agents. Its unique chemical structure allows for the development of new compounds with potent antibacterial properties, which can be useful in the fight against antibiotic-resistant bacteria.
Used in Antitumor Applications:
4,6-Dimethoxyindole is used as a reactant for the preparation of pyridocarbazoles and pyrrolocarbazole analogs, which have been shown to possess anti-tumor activity. These compounds can potentially be developed into new therapeutic agents for the treatment of various types of cancer.
Used in Neuropharmacology:
4,6-Dimethoxyindole is used as a reactant for the preparation of methoxy-substituted N1-benzenesulfonylindole analogs, which act as human 5-HT6 serotonin receptor ligands. These compounds can modulate the activity of the 5-HT6 receptor, making them potential candidates for the development of drugs targeting neurological and psychiatric disorders.

InChI:InChI=1/C10H11NO2/c1-12-7-5-9-8(3-4-11-9)10(6-7)13-2/h3-6,11H,1-2H3

Upstream product

• 107-21-1 ethylene glycol 
• 10272-07-8 3.5-dimethoxyaniline 
• 23659-85-0 ethyl 3-hydroxy-4,6-dimethoxylindolin-2-one-3-carboxylate 

Downstream Products

• 1421942-24-6 3-acetyl-4,6-dimethoxy-1-(2,4-dichlorobenzyl)-1H-indole 
• 1421942-32-6 4-[1-(2,4-dichlorobenzyl)-4,6-dimethoxy-1H-indol-3-yl]-2-hydroxy-4-oxobut-2-enoic acid 
• 1421942-28-0 ethyl 4-[1-(2,4-dichlorobenzyl)-4,6-dimethoxy-1H-indol-3-yl]-2-hydroxy-4-oxobut-2-enoate 
• 1269920-20-8 4-[1-(4-fluorobenzyl)-4,6-dimethoxy-1H-indol-3-yl]-2-hydroxy-4-oxobut-2-enoic acid 
• 1269920-15-1 ethyl 4-[1-(4-fluorobenzyl)-4,6-dimethoxy-1H-indol-3-yl]-2-hydroxy-4-oxobut-2-enoate 
• 1269920-10-6 3-acetyl-4,6-dimethoxy-1-(4-fluorobenzyl)-1H-indole 
• 146255-80-3 1-(3,4-dimethoxybenzoyl)-4,6-dimethoxyindole 
• 146255-78-9 1-(4-chlorobenzoyl)-4,6-dimethoxyindole 
• 146255-77-8 1-(4-methylbenzoyl)-4,6-dimethoxyindole 
• 146255-76-7 1-benzoyl-4,6-dimethoxyindole 
• 146255-82-5 1-(3'-benzyloxy-4'-methoxybenzoyl)-4,6-dimethoxyindole 

Relevant articles and documents

β-Amino alcohols from anilines and ethylene glycol through heterogeneous Borrowing Hydrogen reaction

Borrowing Hydrogen (BH), also called Hydrogen Autotransfer (HA), reaction with neat ethylene glycol represents a key step in the preparation of β-amino alcohols. However, due to the stability of ethylene glycol, mono-activation has rarely been achieved. Herein, a combination of Pd/C and ZnO is reported as heterogeneous catalyst for this BH/HA reaction. This system results in an extremely air and moisture stable, and economic catalyst able to mono-functionalize ethylene glycol in water, without further activation of the diol. In this work, different diols and aromatic amines have been explored affording a new approach towards amino alcohols. This study reveals how the combination of two solid species can afford interesting catalytic properties in heterogeneous phase. ZnO activates ethylene glycol while Pd/C is the responsible of the BH/HA cycle. This catalytic system has also been found useful to dehydrogenate indoles affording indolines that undergo in situ BH/HA cycle prior to re-aromatization, representing a tandem heterogeneous process.

Metal Template Reactions. XX. Macrocyclic Metal Complexes Derived from 4,6-Dimethoxy-3-methylindole-2,7-dicarbaldehyde and Some Primary Diamines with Additional Nitrogen Donor Atoms

4,6-Dimethoxy-3-methylindole-2,7-dicarbaldehyde (6) has been prepared by the formylation of 4,6-dimethoxy-3-methylindole (5), itself prepared by the hydride reduction of the oxoindole (4).Macrocyclic nickel(II) and copper(II) complexes (8), (10) and (12) have been prepared from the dialdehyde (6), the apprppriate metal(II) acetate and the primary diamines 2,2'-iminobisaniline (7), 2-amino-N-(2'-aminophenyl)benzamide (9) and 2-amino-N-(2'-aminobenzoyl)benzamide (11) respectively.

SYNTHESIS OF MACROCYCLIC LIGANDS CONTAINING THE INDOLE RING SYSTEM

2,7-Diformyl-3-methyl-4,6-dimethoxyindole (6) has been synthesized and converted by metal template reactions into the macrocyclic complexes (10-12).