14430-23-0

Basic information

• Product Name: 5,6-DIMETHOXYINDOLE
• Synonyms: 5,6-Dimethoxyindole,99%;5,6-Dimethoxy-1H-indole 99%;5,6-Dimethoxy-1H-indole99%;AKOS JY2083477;5,6-DIMETHOXYINDOLE;5,6-DIMETHOXY-1H-INDOLE;1H-Indole, 5,6-dimethoxy-;5,6-Dimethoxyindole 99%
• CAS NO: 14430-23-0
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• EINECS: 238-402-5
• Product Categories: Amines;Aromatics;Indoles and derivatives;Indoline & Oxindole;Heterocyclic Compounds;Indole Derivatives;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 14430-23-0.mol
• Article Data: 25

Chemical Properties

• Melting Point: 154-157 °C(lit.)
• Boiling Point: 198°C 8mm
• Flash Point: 198°C/8mm
• Appearance: Beige/Powder
• Density: 1.182 g/cm³
• Vapor Pressure: 0.0006mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 16.93±0.30(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 5683
• CAS DataBase Reference: 5,6-DIMETHOXYINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIMETHOXYINDOLE(14430-23-0)
• EPA Substance Registry System: 5,6-DIMETHOXYINDOLE(14430-23-0)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 14430-23-0(Hazardous Substances Data)

Usage

Description

5,6-DIMETHOXYINDOLE is an indole derivative characterized by its beige powder appearance. It is known for its analgesic and anti-inflammatory properties, making it a valuable compound in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
5,6-DIMETHOXYINDOLE is used as a reactant for the synthesis of various pharmaceutical compounds due to its versatile chemical properties. It plays a crucial role in the development of new drugs and therapies.
5,6-DIMETHOXYINDOLE is used as a reactant for the synthesis of N-benzyl-N-cyclopropyl-5,6-dimethoxyindole-3-glyoxalamide, which is an important compound in the development of new pharmaceuticals.
Used in Synthesis of Indolylhydroxyoxindoles:
5,6-DIMETHOXYINDOLE is used as a reactant in the synthesis of indolylhydroxyoxindoles via enantioselective Friedel-Crafts reaction. This application is significant in the production of chiral compounds, which are essential in the pharmaceutical industry.
Used in Synthesis of Benzyl Trimethoxyindoles:
5,6-DIMETHOXYINDOLE is used as a reactant in the synthesis of benzyl trimethoxyindoles, which are important intermediates in the production of various pharmaceutical compounds.
Used in Synthesis of HIV-1 Inhibitors:
5,6-DIMETHOXYINDOLE is used as a reactant for the synthesis of benzoylpiperazinyl-indolyl ethane dione derivatives, which are known as HIV-1 inhibitors. This application highlights its potential in the development of antiretroviral drugs.
Used in Synthesis of Antitumor Agents:
5,6-DIMETHOXYINDOLE is used as a reactant for the synthesis of 1-aroylindole 3-aroylindoles, which are combretastatin A-4 analogs. These compounds serve as antitumor agents and tubulin polymerization inhibitors, making them valuable in cancer research and treatment.
Used in Preparation of Tryptophanol Derivatives:
5,6-DIMETHOXYINDOLE is used as a reactant for the preparation of tryptophanol derivatives via the Grignard reaction. This application is important in the synthesis of various biologically active compounds, further expanding the utility of 5,6-DIMETHOXYINDOLE in the pharmaceutical industry.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 5887, 1953 DOI: 10.1021/ja01119a030Synthesis of 5,6-Dimethoxyindoles and 5,6-Dimethoxyoxindoles. A New Synthesis of Indoles DOI: 10.1021/ja01619a049

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

Upstream product

• 15937-07-2 5,6-dimethoxyindoline 
• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 20357-25-9 6-nitroveratraldehyde 
• 107-21-1 ethylene glycol 
• 6315-89-5 3,4-dimethoxyaniline 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 63375-81-5 2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine 
• 65907-71-3 1,2-dimethoxy-4-nitro-5-vinylbenzene 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 3166-78-7 2-(2,4,5-trimethoxyphenyl)ethylamine hydrochloride 
• 125438-24-6 2,4,5-trimethoxybenzaldehyde O-(trimethylsilyl)cyanohydrin 
• 4460-86-0 asaraldehyde 
• 106103-12-2 2,2,2-Trifluoro-N-[2-(2,4,5-trimethoxy-phenyl)-ethyl]-acetamide 
• 74054-31-2 methyl 2-bromo-4,5-dimethoxyphenethylcarbamate 

Downstream Products

• 102948-01-6 (5,6-dimethoxy-indol-3-yl)-glyoxylic acid dibenzylamide 
• 5446-82-2 5,6-dimethoxygramine 
• 142683-35-0 methyl N-(diphenylmethylene)-5,6-dimethoxytryptophanate 
• 4722-81-0 AG 1693 
• 142683-49-6 1,1-diphenyl-3-carbomethoxy-6,7-dimethoxy-1,2,3,4-tetrahydro-β-carboline 
• 3131-52-0 1H-indole-5,6-diol 
• 1068439-32-6 5,6-dimethoxy-1-(phenylsulfonyl)-1H-indole 

Relevant articles and documents

Method for preparing 5, 6-dihydroxyindole by using modified ordered mesoporous carbon supported metal catalyst

The invention belongs to the technical field of organic synthesis, and discloses a method for preparing 5, 6-dihydroxyindole by using a modified ordered mesoporous carbon supported metal catalyst. According to the invention, phenolic resin is taken as a carbon source, polyether F127 is taken as a soft template, an ordered mesoporous carbon loaded metal material is prepared as a catalyst, and high catalytic activity and good stability are shown in the reaction of 3, 4-dimethoxyaniline and ethylene glycol. The catalyst prepared by the method has remarkable effects of avoiding agglomeration and stripping of active components, improving the reaction catalytic activity and prolonging the service life. The raw materials are easy to obtain, the cost is low, the product is white powder, the product purity reaches 98.3%, the ethylene glycol conversion rate in the reaction is close to 60%, the selectivity of the 5, 6-dimethoxy indole reaches 85% or above, and the final yield of the 5, 6-dihydroxy indole can reach 81% or above.

Tandem Wittig – Reductive annulation decarboxylation approach for the synthesis of indole and 2-substituted indoles

A simple tandem Wittig reaction-reductive decarboxylation route is established for the synthesis of indoles from commercially available o-nitrobenzaldehydes and a stable phosphorane. The method allows access to indoles in a very fast manner without involving any metal or expensive reagents or inert atmosphere. Also 2-substituted indoles are obtained which forms an important core of many biological active compounds.

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.