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

Chemical Properties

Beige powder

Uses

5,6-Dimethoxyindole is an indole derivative as analgesic antiinflammatory. It was used in the synthesis of N-benzyl-N-cyclopropyl-5,6-dimethoxyindole-3-glyoxalamide.

Application

5,6-Dimethoxyindole was used in the synthesis of N-benzyl-N-cyclopropyl-5,6-dimethoxyindole-3-glyoxalamide.Reactant in synthesis of indolylhydroxyoxindoles via enantioselective Friedel-Crafts reactionReactant in synthesis of benzyl trimethoxyindolesReactant for synthesis of benzoylpiperazinyl-indolyl ethane dione derivatives as HIV-1 inhibitorsReactant for synthesis of 1-aroylindole 3-aroylindoles combretastatin A-4 analogs as antitumor agents and tubulin polymerization inhibitorsReactant for preparation of tryptophanol derivatives via the Grignard reaction

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

• 88210-96-2 5,6-dimethoxyindole-2-carboxylic acid 
• 17354-04-0 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile 
• 50546-80-0 (2-amino-4,5-dimethoxy-phenyl)-acetonitrile 
• 106103-20-2 5,5,6-Trimethoxy-3,5-dihydro-2H-indole 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 15937-10-7 1-acetyl-2,3-dihydro-5,6-dimethoxy-1H-indole 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 20357-25-9 6-nitroveratraldehyde 
• 65907-71-3 1,2-dimethoxy-4-nitro-5-vinylbenzene 
• 107-21-1 ethylene glycol 
• 6315-89-5 3,4-dimethoxyaniline 
• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 157670-07-0 2-azido-3-(3',4'-dimethoxyphenyl)acrylic acid methyl ester 
• 77-78-1 dimethyl sulfate 

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 
• 15937-07-2 5,6-dimethoxyindoline 
• 181184-12-3 5,6-dimethoxy-3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole 
• 181184-17-8 5,6-dimethoxy-3-(1-benzyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole 
• 480436-00-8 3-(5,6-dimethoxy-1H-indol-3-yl)-2,5-dichloro[1,4]benzoquinone 
• 572-67-8 isoreserpiline 
• 131-02-2 reserpiline 
• 57330-45-7 5,6-dimethoxy-2-methyl-1H-indole 
• 1269920-11-7 3-acetyl-5,6-dimethoxy-1-(4-fluorobenzyl)-1H-indole 
• 1269920-16-2 ethyl 4-[1-(4-fluorobenzyl)-5,6-dimethoxy-1H-indol-3-yl]-2-hydroxy-4-oxobut-2-enoate 
• 1269920-21-9 4-[1-(4-fluorobenzyl)-5,6-dimethoxy-1H-indol-3-yl]-2-hydroxy-4-oxobut-2-enoic acid 

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.