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

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

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

• 88210-96-2 5,6-dimethoxyindole-2-carboxylic acid 
• 77-78-1 dimethyl sulfate 
• 20357-25-9 6-nitroveratraldehyde 
• 65907-71-3 1,2-dimethoxy-4-nitro-5-vinylbenzene 
• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 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 
• 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 

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 
• 480436-00-8 3-(5,6-dimethoxy-1H-indol-3-yl)-2,5-dichloro[1,4]benzoquinone 
• 57330-45-7 5,6-dimethoxy-2-methyl-1H-indole 
• 142769-27-5 5,6-dimethoxy-1H-indole-3-carbaldehyde 
• 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 
• 15937-07-2 5,6-dimethoxyindoline 
• 3131-52-0 1H-indole-5,6-diol 

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.

Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes

An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.

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.

Straight Access to Indoles from Anilines and Ethylene Glycol by Heterogeneous Acceptorless Dehydrogenative Condensation

The development of original strategies for the preparation of indole derivatives is a major goal in drug design. Herein, we report the first straight access to indoles from anilines and ethylene glycol by heterogeneous catalysis, based on an acceptorless dehydrogenative condensation, under noninert conditions. In order to achieve high selectivity, a combination of Pt/Al2O3 and ZnO have been found to slowly dehydrogenate ethylene glycol generating, after condensation with the amine and tautomeric equilibrium, the corresponding pyrrole-ring unsubstituted indoles.

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.

Catalytic synthesis method of indole compounds

The invention discloses a catalytic synthesis method of indole compounds.The method includes the following steps of firstly, conducting stirring reaction on ortho-nitrostyrolene or derivatives of ortho-nitrostyrolene, bis(pinacolato)diboron, alkali and low-grade saturated monohydric alcohol under the atmosphere of nitrogen; secondly, cooling the reaction product in the first step to the room temperature, adding ethyl acetate to be sufficiently mixed, and washing with ethyl acetate after filtering; thirdly, spin-drying low-grade saturated monohydric alcohol in an organic phase of the material obtained in the second step, passing through a silica gel column, and drip washing the silica gel column with eluent composed of petroleum ether and ethyl acetate to obtain pure products, namely, the indole compounds.By means of the method, under the neutral conditions, bis(pinacolato)diboron low in price serves as the raw material, friendly low-grade saturated monohydric alcohol serves as the solvent, the indole compounds are obtained through simple operation, the raw materials are low in price and easy to obtain, efficiency and safety are high, and wide expandability and good industrial application prospects are achieved.

Active and Recyclable Catalytic Synthesis of Indoles by Reductive Cyclization of 2-(2-Nitroaryl)acetonitriles in the Presence of Co-Rh Heterobimetallic Nanoparticles with Atmospheric Hydrogen under Mild Conditions

A cobalt-rhodium heterobimetallic nanoparticle-catalyzed reductive cyclization of 2-(2-nitroaryl)acetonitriles to indoles has been achieved. The tandem reaction proceeds without any additives under the mild conditions (1 atm H2 and 25 °C). This procedure could be scaled up to the gram scale. The catalytic system is significantly stable under these reaction conditions and could be reused more than ten times without loss of catalytic activity.

Phosphane-free Pd0-catalyzed cycloamination and carbonylation with Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3: Preparation of benzocyclic amines and benzolactams

Phosphane-free Pd0-catalyzed intramolecular aromatic amination was studied. o-Halophenethylamines and 3-(o-halophenyl)propylamines were found to be transformed into indolines and quinolines in a catalytic system based on Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3. Application of the method to substrates containing isoquinoline rings- the 1-(o-bromobenzyl)-3,4-dihydroisoquinolines 6, the 1-(o-bromobenzyl)-1,2,3,4-tetrahydroisoquinolines 7, and the 1-(o-bromophenethyl)isoquinolines 9- provided the indolo[2,1-a]isoquinoline and dibenzo[a,f]quinolizine ring systems 8 and 10. Extension of the method to β-carbolines (compounds 11, 12, and 17) produced the benz[f]indolo[2,3-a] indolizine-13-ones 15 and the benz[f]indolo[2,3-a]quinolizine 18. The benzo[f]pyrido[3,4-a]indolizine and indolo[f]pyrido[3,4-a]indolizin-12-one ring systems 27 and 31 were built in a similar manner. It was also found that under an atmosphere of CO the same catalytic system produced the corresponding benzolactams, the isoquino[2,1-a][2,7]naphthyridine 34 and the indolo[2,3-a]pyrido[g]quinolizin-8-one 36 [(±)-dihydronauclefine] in good yields. Copyright

Concise, efficient and practical assembly of bromo-5,6-dimethoxyindole building blocks

A concise, efficient and simple route to a series of bromoindole building blocks is described. The synthetic routes are highlighted by purification-free preparation of o-nitrocinnamate intermediates and clean, modified Cadogan indole syntheses. The scope of this indole synthesis has been explored and expanded through the use of a range of solvents and easily removable phosphine reagents.

Effects of indole fatty alcohols on the differentiation of neural stem cell derived neurospheres

In a search for inducers of neuronal differentiation to treat neurodegenerative diseases such as Alzheimer's disease, a series of indole fatty alcohols (IFAs) were prepared, 13c (n = 18) was able to promote the differentiation of neural stem cell derived neurospheres into neurons at a concentration of 10 nM. Analysis of the expression of the Notch pathway genes in neurospheres treated during the differentiation phase with 13c (n = 18) revealed a significant decrease in the transcription of the Notch 4 receptor.