61675-19-2

Basic information

• Product Name: 5-METHOXY-3-(2-NITROVINYL)-INDOL
• Synonyms: 5-METHOXY-3-(2-NITROVINYL)-INDOL;5-METHOXY-3-(2-NITROVINYL)-INDOLE;5-METHOXYINDOLE-3-NITRO VINYL;5-Methoxy-3-(2μ-nitroethenyl)indole;NSC 88875;5-Methoxy-3-(2-nitrovinyl)-1H-indole;(E)-5-methoxy-3-(2-nitrovinyl)-1H-indole
• CAS NO: 61675-19-2
• Molecular Formula: C₁₁H₁₀N₂O₃
• Molecular Weight: 218.21
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Indoles;C11;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 61675-19-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 159-160 °C
• Boiling Point: 438.5 °C at 760 mmHg
• Flash Point: 219 °C
• Appearance: /
• Density: 1.337 g/cm³
• Vapor Pressure: 1.77E-07mmHg at 25°C
• Refractive Index: 1.691
• PKA: 15.34±0.30(Predicted)
• CAS DataBase Reference: 5-METHOXY-3-(2-NITROVINYL)-INDOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-3-(2-NITROVINYL)-INDOL(61675-19-2)
• EPA Substance Registry System: 5-METHOXY-3-(2-NITROVINYL)-INDOL(61675-19-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 61675-19-2(Hazardous Substances Data)

Usage

Description

5-METHOXY-3-(2-NITROVINYL)-INDOL is an organic compound with the molecular formula C11H10N2O3. It is a derivative of indole, which is a heterocyclic aromatic organic compound. 5-METHOXY-3-(2-NITROVINYL)-INDOL is characterized by the presence of a nitrovinyl group and a methoxy group attached to the indole structure, which may contribute to its potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
5-METHOXY-3-(2-NITROVINYL)-INDOL is used as a reactant for the preparation of inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2). These inhibitors play a crucial role in regulating cellular processes such as inflammation, cell growth, and apoptosis, making them important targets for the development of therapeutic agents.
Used in Chemical Industry:
5-METHOXY-3-(2-NITROVINYL)-INDOL is used as a reactant for the synthesis of indole lipoic acid derivatives. These derivatives exhibit antioxidant properties and are effective against lipid peroxidation, a process that can lead to cellular damage and contribute to various diseases, including cardiovascular and neurodegenerative disorders.
Used in Biotechnology Industry:
5-METHOXY-3-(2-NITROVINYL)-INDOL is used as a reactant for the preparation of indole ethylamine derivatives. These derivatives have been found to act as melatonin analogs, which are important for regulating sleep-wake cycles, mood, and other physiological processes. The development of melatonin analogs can be useful in the treatment of sleep disorders and other conditions related to the circadian rhythm.

InChI:InChI=1/C11H10N2O3/c1-16-9-2-3-11-10(6-9)8(7-12-11)4-5-13(14)15/h2-7,12H,1H3/b5-4-

Upstream product

• 10601-19-1 5-methoxyindole-3-carboxaldehyde 
• 75-52-5 nitromethane 
• 1006-94-6 5-methoxylindole 
• 73430-27-0 1-dimethylamino-2-nitroethene 
• 104-94-9 4-methoxy-aniline 
• 73430-27-0 (E)-N,N-dimethyl-2-nitroethenamine 

Downstream Products

• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 73-31-4 5-methoxy-N-acetyl-tryptamine 
• 66012-82-6 N-Propionyl-5-methoxytryptamine 
• 3589-72-8 6-methoxyharman 
• 1554471-88-3 2-bromo-4-(1-(5-methoxy-1H-indol-3-yl)-2-nitroethyl)aniline 
• 847851-60-9 C₂₂H₂₆N₂O₂ 
• 1631136-28-1 C₂₉H₃₂N₂O₂ 
• 1020701-51-2 N-(2-{5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)acetamide 
• 67199-10-4 methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate 

Relevant articles and documents

Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source

A safe, practical and eco-friendly electrochemical methodology for the synthesis of 3-formylated indoles has been developed by the utilization of Me3N as a novel formylating reagent. Stoichiometric oxidants, metal catalysts, and activating agents were avoided in this method, and an aqueous biphasic system ofn-Bu4NBF4/PEG-400/H2O was used as a recyclable and reusable reaction medium, which made this electrosynthesis approach more sustainable and environmentally friendly. This process expanded the substrate scope and functional group tolerance for bothN-EDG andN-EWG indoles. Furthermore, late-stage functionalization and total/formal synthesis of drugs and natural products were realized by means of this route.

Metal-Free Dearomatization: Direct Access to Spiroindol(en)ines in Batch and Continuous-Flow

A metal-free, phosphine-catalyzed intramolecular “umpolung Michael addition” on alkynes to form spiroindol(en)ines is reported. This nucleophilic catalysis enables the formation of a wide scope of five- and six-membered spiroindol(en)ines in moderate to excellent yields in batch as well as under continuous-flow conditions. Triphenylphosphine-catalyzed nucleophilic activation of alkynes allows the exclusive formation of exo-product under mild reaction conditions.

An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives

An environmentally friendly and efficient protocol (KX/oxone) for oxidative halocyclization of tryptamine/tryptophol derivatives was developed and demonstrated with 28 examples and concise total synthesis of cyclotryptamine alkaloid protubonines A and B. The distinct advantage of this protocol over all previous methods is that no organic byproduct is generated from a halogenating agent or oxidant, thus greatly reducing the environmental impact of halocyclization and facilitating the post-reaction purification.