4560-13-8

Basic information

• Product Name: dimethyl-[2-(2-phenyl-indol-3-yl)-ethyl]-amine
• Synonyms: dimethyl-[2-(2-phenyl-indol-3-yl)-ethyl]-amine
• CAS NO: 4560-13-8
• Molecular Weight: 264.37
• Mol File: 4560-13-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: dimethyl-[2-(2-phenyl-indol-3-yl)-ethyl]-amine(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl-[2-(2-phenyl-indol-3-yl)-ethyl]-amine(4560-13-8)
• EPA Substance Registry System: dimethyl-[2-(2-phenyl-indol-3-yl)-ethyl]-amine(4560-13-8)

Safety Data

• Hazardous Substances Data: 4560-13-8(Hazardous Substances Data)

Upstream product

• 98-80-6 phenylboronic acid 
• 61-50-7 N,N-dimethyltryptamine 
• 591-50-4 iodobenzene 
• 3760-63-2 4-(dimethylamino)-1-phenylbutan-1-one 
• 100-63-0 phenylhydrazine 
• 948-65-2 2-phenyl-indole 
• 221283-98-3 1-tert-butoxycarbonyl-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-indole 
• 1217-80-7 2-(2-phenyl-1H-indol-3-yl)ethylamine 
• 74-88-4 methyl iodide 
• 132594-38-8 (2-phenyl-indol-3-yl)-glyoxylic acid dimethylamide 

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.

A versatile linkage strategy for solid-phase synthesis of N,N-dimethyltryptamines and β-carbolines

(matrix presented) Various tryptamines are captured by a vinylsulfonylmethyl polystyrene resin, generating a safety-catch linkage. β-Carbolines can be formed from 4 by a Pictet-Spengler reaction with the introduction of R1. Tryptamine 4 can also be derivatized by acylation or copper-mediated coupling to introduce R2. If X = Br, Suzuki coupling can be used to introduce R3. After derivatization, the indole derivatives are activated with methyl iodide and released under mild basic condition.