1217-80-7

Basic information

• Product Name: 2-(2-PHENYL-1H-INDOL-3-YL)-ETHYLAMINE
• Synonyms: RARECHEM AL BW 0922;2-(2-PHENYL-1H-INDOL-3-YL)-ETHYLAMINE;2-(2-Phenyl-1H-indol-3-yl)ethanaMine
• CAS NO: 1217-80-7
• Molecular Formula: C₁₆H₁₆N₂
• Molecular Weight: 236.31
• Mol File: 1217-80-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 69-72 °C
• Boiling Point: 468.6±33.0 °C(Predicted)
• Appearance: /
• Density: 1.160±0.06 g/cm3(Predicted)
• PKA: 17.00±0.30(Predicted)
• CAS DataBase Reference: 2-(2-PHENYL-1H-INDOL-3-YL)-ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-PHENYL-1H-INDOL-3-YL)-ETHYLAMINE(1217-80-7)
• EPA Substance Registry System: 2-(2-PHENYL-1H-INDOL-3-YL)-ETHYLAMINE(1217-80-7)

Safety Data

• Hazardous Substances Data: 1217-80-7(Hazardous Substances Data)

Usage

General Description

2-(2-Phenyl-1H-indol-3-yl)-ethylamine, also known as 3-(2-aminioethyl)indole or 3C-E, is a chemical compound that belongs to the class of substituted phenethylamines. It is a psychedelic drug with hallucinogenic and stimulant effects, and is structurally related to the amphetamine and phenethylamine families. 3C-E is a potent agonist for the 5-HT2A receptor, which is a subtype of serotonin receptor in the brain, leading to its hallucinogenic properties. It is also known for its potential to produce altered perception, thought, and emotion. However, 3C-E's potential for causing adverse effects and dependence has raised concerns about its use as a recreational drug.

Upstream product

• 122631-43-0 (E)-3-(2-nitrovinyl)-2-phenyl-1H-indole 
• 61-54-1 tryptamine 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 1225-93-0 2-phenyl-3-(2-nitrovinyl)-1H-indole 
• 591-50-4 iodobenzene 
• 27005-52-3 2-(2-phenyl-1H-indol-3-yl)acetonitrile 
• 100-63-0 phenylhydrazine 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 25365-71-3 2-phenyl-1H-indol-3-carboxaldehyde 
• 15741-71-6 N-phthalimidotryptamine 
• 948-65-2 2-phenyl-indole 
• 98-80-6 phenylboronic acid 
• 192182-46-0 2-(2-(2-bromo-1H-indol-3-yl)ethyl)isoindoline-1,3-dione 
• 408310-88-3 2-oxo-2-(2-phenyl-1H-indol-3-yl)-acetamide 

Downstream Products

• 4560-13-8 dimethyl-[2-(2-phenyl-indol-3-yl)-ethyl]-amine 
• 1370733-02-0 C₁₉H₂₀N₂O₂ 
• 1370733-39-3 N-methyl-2-(2-phenyl-1H-indol-3-yl)ethanamine 
• 1370733-40-6 C₁₈H₁₈N₂O 
• 1370733-41-7 C₁₇H₁₇BrN₂ 
• 1416352-98-1 4-methyl-N-(2-(2-phenyl-1H-indol-3-yl)-ethyl)benzenesulfonamide 
• 1616347-90-0 2-phenyl-2'-methylene-1'-tosylspiro[indole-3,4'-piperidine] 
• 192182-30-2 2-(2-(2-phenyl-1H-indol-3-yl)ethyl)isoindoline-1,3-dione 
• 1180-76-3 2'-furan-2-yl-2-phenyl-1'-(toluene-4-sulfonyl)-1,2-dihydro-spiro[indole-3,3'-pyrrolidine] 

Relevant articles and documents

Pd(II)-Catalyzed Intramolecular C(sp2)-H Arylation of Tryptamines Using the Nonsteric NH2as a Directing Group

The free amine-directed C-H functionalization reactions are challenging and mainly restricted to bulky amines. In this work, we report the nonsteric NH2-directed Pd(II)-catalyzed intramolecular C(sp2)-H arylation of tryptamines, which enables the efficient, gram-scale, and regioselective synthesis of versatile 2-aryltryptamines (35 examples, up to 98% yield). This approach broadens the substrate scope of the free amine-directed C-H functionalization, not limited to bulky amine substrates. Late-stage elaborations of 2-aryltryptamines achieve the divergent construction of the complex core structures that are prevalent in highly valuable natural products such as aurantioclavine, chimonanthine, and phalarine.

Access to 2-Arylindoles via Decarboxylative C?C Coupling in Aqueous Medium and to Heteroaryl Carboxylates under Base-Free Conditions using Diaryliodonium Salts

Easily accessible heteroaromatic carboxylic acids and diaryliodonium salts were successfully employed to construct valuable 2-arylindoles and heteroaryl carboxylates in a regioselective fashion. C2-arylated indoles were produced using a Pd-catalyzed decarboxylative strategy in water without any base, oxidant, or ligand. Heteroaryl carboxylates were prepared under metal and base-free conditions. This protocol was successfully utilized to synthesize Paullone, a cyclin-dependent kinase (CDK) inhibitor.

Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate

We report the intermolecular palladium-catalyzed reaction of tert-butyl propargyl carbonate with tryptamine derivatives or other indole-containing bis-nucleophiles. The reaction proceeds under mild conditions and with low catalyst loadings to afford novel spiroindolenine products in good to high yields.