203394-30-3

Basic information

• Product Name: 2-(1H-INDOL-3-YL)-2-(4-METHOXY-PHENYL)-ETHYLAMINE
• Synonyms: AKOS BBS-00001426;2-(1H-INDOL-3-YL)-2-(4-METHOXYPHENYL)ETHANAMINE;2-(1H-INDOL-3-YL)-2-(4-METHOXY-PHENYL)-ETHYLAMINE;BAS 01057227;Oprea1_359818;Oprea1_648254;ST5006766
• CAS NO: 203394-30-3
• Molecular Formula: C₁₇H₁₈N₂O
• Molecular Weight: 266.34
• Mol File: 203394-30-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(1H-INDOL-3-YL)-2-(4-METHOXY-PHENYL)-ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1H-INDOL-3-YL)-2-(4-METHOXY-PHENYL)-ETHYLAMINE(203394-30-3)
• EPA Substance Registry System: 2-(1H-INDOL-3-YL)-2-(4-METHOXY-PHENYL)-ETHYLAMINE(203394-30-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 203394-30-3(Hazardous Substances Data)

Usage

Structure

Contains an indole and a methoxyphenyl group

Classification

Amine derivative

Potential applications

Medicinal chemistry, due to structural relation to neurotransmitters and alkaloids

Research focus

Pharmacological properties, use as a building block for synthesis of biologically active molecules

Interest

Potential role as a precursor to other indoleand phenyl-based compounds in organic synthesis.

Upstream product

• 33723-33-0 3-[1-(4-methoxyphenyl)-2-nitroethyl]-1H-indole 
• 120-72-9 indole 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 5953-85-5 p-anisaldehyde hydrazone 
• 1610542-31-8 1-[(Z)-2-fluoro-2-nitroethenyl]-4-(methyloxy)benzene 
• 3179-10-0 (E)-1-methoxy-4-(2-nitrovinyl)benzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 402490-62-4 1-bromo-1-fluoro-2-(4-methoxy-phenyl)-ethylene 

Relevant articles and documents

The base-free van Leusen reaction of cyclic imines on water: Synthesis of N-fused imidazo 6,11-dihydro β-carboline derivatives

Construction of imidazoles has been demonstrated on water under base-free conditions. The reaction of dihydro β-carboline imines and p-toluenesulfonylmethyl isocyanides furnished the corresponding substituted N-fused imidazo 6,11-dihydro β-carboline derivatives in very good yields under ambient conditions. The use of deuterium oxide (D2O) as a solvent enabled the incorporation of deuterium isotopes in the imidazole ring.

Green, Catalyst-Free Reaction of Indoles with β-Fluoro-β-nitrostyrenes in Water

The reaction of 2-fluoro-2-nitrostyrenes with various indoles was investigated. We found that the reaction proceeds as a Michael addition in a highly regioselective manner to form 3-(1-aryl-2-fluoro-2-nitroethyl)-1H-indoles. Thus, a green and catalyst-free synthesis of these compounds was developed using water as a reaction medium. The high effectiveness of this approach was demonstrated through the preparation of target products in up to 92 % isolated yield. Subsequent reduction of the nitro group was investigated. We found that due to the instability of the intermediate α-fluoro amines, the reduction led to non-fluorinated tryptamine derivatives.

Ionic liquid-coordinated ytterbium(III) sulfonate catalyzed michael addition of indoles to electron-deficient nitroolefins

The Michael addition of indoles to electron-deficient nitroolefins was effectively catalyzed by an ionic liquid-coordinated ytterbium(III) sulfonate catalyst. The recycling procedure of the catalyst was very simple without extraction with water, and the c

Synthesis of 4-(p-methoxyphenyl)-β-carboline, a new inhibitor of cellular calcium influx

4-(p-methoxyphenyl)-β-carboline was prepared in four steps from indole. The key step involved palladium-catalyzed dehydrogenation of a dihydro-β- carboline dichlorophosphinic acid salt. The success of the dehydrogenation was found to depend on the catalys