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

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

Downstream Products

• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 73-31-4 5-methoxy-N-acetyl-tryptamine 
• 67199-10-4 methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate 
• 1020701-51-2 N-(2-{5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)acetamide 
• 1631136-28-1 C₂₉H₃₂N₂O₂ 
• 847851-60-9 C₂₂H₂₆N₂O₂ 
• 1554471-88-3 2-bromo-4-(1-(5-methoxy-1H-indol-3-yl)-2-nitroethyl)aniline 
• 3589-72-8 6-methoxyharman 
• 66012-82-6 N-Propionyl-5-methoxytryptamine 
• 20731-70-8 5-methoxy-α-methyltryptamine 
• 947767-16-0 C₁₈H₂₀N₂O 

Relevant articles and documents

Method for synthesizing melatonin intermediate by taking methoxyphenamine as raw material

The invention belongs to the technical field of compound synthesis, and aims to solve the problem that expensive reducing agents are needed in the present method for synthesizing melatonin, and the cost is high. The invention provides a method for synthesizing melatonin intermediate by taking methoxyphenamine as a raw material, and the like. Pt / Al with supported catalyst by taking methoxyaniline and ethylene glycol as raw materials2 O3 One-step hydrothermal method synthesizes 5 - methoxyindole and then obtains melatonin precursor 3 methoxytryptamine by 5 -step hydrothermal reaction. 5 - Methoxyindole is firstly synthesized by taking ethylene glycol and paramethoxyaniline as raw materials, then 3 methoxytryptamine is obtained through 5 - steps, and the total yield of the reaction is 14.0%. final synthesis of melatonin. A new melatonin synthesis route is designed, and the melatonin precursor 5 - methoxytryptamine is synthesized by using a raw material aniline derivative and ethylene glycol which are simple in application structure and low in cost.

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.

Revision of the Structure and Total Synthesis of Topsentin C

An efficient synthetic approach to access (indol-3-yl)ethane-1,2-diamines with a protecting group at the indole N atom from readily available 3-(2-nitrovinyl)indoles is reported. This approach includes solvent-free conjugate addition of O-pivaloylhydroxylamines to 1-Boc-3-(2-nitrovinyl)indoles followed by mild reduction of the adducts. The obtained (indol-3-yl)ethane-1,2-diamines are convenient synthetic precursors for several classes of marine alkaloids. The first total synthesis of racemic topsentin C, a secondary metabolite from Hexadella sp., based on this approach is reported. The initially proposed structure for topsentin C has been revised.