28059-24-7

Basic information

• Product Name: METHYL 5,6-DIMETHOXY-1H-INDOLE-2-CARBOXYLATE
• Synonyms: METHYL 5,6-DIMETHOXY-1H-INDOLE-2-CARBOXYLATE;AKOS JY2083082;Methyl 5,6-Dimethoxyindole-2-carboxylate
• CAS NO: 28059-24-7
• Molecular Formula: C₁₂H₁₃NO₄
• Molecular Weight: 235.24
• Mol File: 28059-24-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 167-168 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• Boiling Point: 390.2°C at 760 mmHg
• Flash Point: 189.8°C
• Appearance: /
• Density: 1.252g/cm³
• Vapor Pressure: 2.69E-06mmHg at 25°C
• Refractive Index: 1.593
• PKA: 14.90±0.30(Predicted)
• CAS DataBase Reference: METHYL 5,6-DIMETHOXY-1H-INDOLE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 5,6-DIMETHOXY-1H-INDOLE-2-CARBOXYLATE(28059-24-7)
• EPA Substance Registry System: METHYL 5,6-DIMETHOXY-1H-INDOLE-2-CARBOXYLATE(28059-24-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 28059-24-7(Hazardous Substances Data)

Usage

General Description

Methyl 5,6-dimethoxy-1H-indole-2-carboxylate is a chemical compound with the molecular formula C13H15NO4. It is a derivative of the naturally occurring indole compound and is commonly used in the pharmaceutical industry as a building block for the synthesis of various pharmaceutical drugs. The compound has been found to exhibit a wide range of biological activities, including anti-inflammatory, anti-bacterial, and antiviral properties. It is also used in the field of organic chemistry as a reagent for the synthesis of complex organic molecules. Its unique structure and versatile reactivity make it a valuable tool for medicinal and synthetic chemistry research.

InChI:InChI=1/C12H13NO4/c1-15-10-5-7-4-9(12(14)17-3)13-8(7)6-11(10)16-2/h4-6,13H,1-3H3

Upstream product

• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 886854-07-5 2-(2,2-dibromovinyl)-4,5-dimethoxyphenylamine 
• 855162-94-6 C₁₂H₁₃NO₆ 
• 20357-25-9 6-nitroveratraldehyde 
• 4305-32-2 5-hydroxy-6-methoxy-indole-2-carboxylic acid methyl ester 
• 74-88-4 methyl iodide 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 186581-53-3 diazomethane 
• 10131-14-3 methyl 5,6-dihydroxy-1H-indole-2-carboxylate 
• 157670-07-0 2-azido-3-(3',4'-dimethoxyphenyl)acrylic acid methyl ester 
• 690639-23-7 methyl 2-azido-3-(3',4'-dimethoxyphenyl)-propenoate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 118292-37-8 5,6,7-trimethoxy-1H-indole-2-carboxylic acid methyl ester 
• 157670-11-6 (R)-6,7-Dimethoxy-1-methyl-2-((S)-1-phenyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline 
• 157670-09-2 2-(5,6-Dimethoxy-1H-indol-3-yl)-2-oxo-N-((S)-1-phenyl-ethyl)-acetamide 
• 157670-10-5 [2-(5,6-Dimethoxy-1H-indol-3-yl)-ethyl]-((S)-1-phenyl-ethyl)-amine 
• 812653-13-7 18-[5,6-dimethoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-octadecan-1-ol 
• 812653-12-6 16-[5,6-dimethoxy-1-(4-methoxybenzenesulfonyl)-1H-indol-3-yl]hexadecan-1-ol 
• 812652-87-2 5,6-dimethoxy-1-(4-methoxybenzenesulfonyl)-1H-indole-3-carbaldehyde 
• 142769-27-5 5,6-dimethoxy-1H-indole-3-carbaldehyde 
• 14430-23-0 5,6-dimethoxyindole 
• 690639-25-9 5,6-dihydroxy-1H-indole-2-carboxylic acid pentafluorophenyl ester 
• 690639-24-8 5,6-dimethoxy-1H-indole-2-carboxylic acid pentafluorophenyl ester 

Relevant articles and documents

Role of solvent, pH, and molecular size in excited-state deactivation of key eumelanin building blocks: Implications for melanin pigment photostability

Ultrafast time-resolved fluorescence spectroscopy has been used to investigate the excited-state dynamics of the basic eumelanin building block 5,6-dihydroxyindole-2-carboxylic acid (DHICA), its acetylated, methylated, and carboxylic ester derivatives, and two oligomers, a dimer and a trimer in the O-acetylated forms. The results show that (1) excited-state decays are faster for the trimer relative to the monomer; (2) for parent DHICA, excited-state lifetimes are much shorter in aqueous acidic medium (380 ps) as compared to organic solvent (acetonitrile, 2.6 ns); and (3) variation of fluorescence spectra and excited-state dynamics can be understood as a result of excited-state intramolecular proton transfer (ESIPT). The dependence on the DHICA oligomer size of the excited-state deactivation and its ESIPT mechanism provides important insight into the photostability and the photoprotective function of eumelanin. Mechanistic analogies with the corresponding processes in DNA and other biomolecules are recognized.

A Bioinspired Synthesis of Polyfunctional Indoles

Polyfunctional indoles bearing substituents at C5 and C6 are prevalent in natural products, pharmaceuticals, agrochemicals, and materials. Owing to the remoteness of the C5 and C6 positions, indoles of this family can be difficult to prepare, and often require multistep syntheses. Herein, we describe a concise process that converts simple derivatives of tyrosine into 5,6-difunctionalized indoles by direct oxidation of C?H, N?H, and O?H bonds. Our work draws inspiration from the biosynthetic polymerization of tyrosine to make melanin pigments, but makes an important departure to provide well-defined indole heterocycles.

Ligand-Free Copper-Catalyzed One-Pot Synthesis of Indole-2-carboxylic Esters

A simple, efficient, and facile synthetic route for the preparation of indole-2-carboxylic esters was described. The cascade reactions of 2-bromobenzaldehyde and glycine ester hydrochloride were promoted by Cu2O and a base to provide the corresponding products in good yields. Commercially available, inexpensive substrates and reagents were employed under mild reaction conditions in this one-pot operation, which is complementary to existing methods for access to 2-substituted indoles.