132554-36-0

Basic information

• Product Name: 1H-Indole, 1,6-dimethyl-2-phenyl-
• CAS NO: 132554-36-0
• Molecular Formula: C16H15N
• Molecular Weight: 221.302
• Mol File: 132554-36-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 1,6-dimethyl-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 1,6-dimethyl-2-phenyl-(132554-36-0)
• EPA Substance Registry System: 1H-Indole, 1,6-dimethyl-2-phenyl-(132554-36-0)

Safety Data

• Hazardous Substances Data: 132554-36-0(Hazardous Substances Data)

Upstream product

• 132554-27-9 3-(4-Methyl-pyridin-2-yl)-1-phenyl-propan-1-one 
• 1094425-17-8 N,N-dimethyl-5-methyl-2-(phenylethynyl)aniline 
• 3420-02-8 6-methylindole 
• 132554-31-5 1,4-Dimethyl-2-(2-benzoylethyl)pyridinium iodide 
• 98-86-2 acetophenone 
• 536-89-0 m-tolylhydrazine 
• 66354-87-8 6-methyl-2-phenyl-1H-indole 
• 74-88-4 methyl iodide 
• 5621-15-8 1,6-dimethyl-1H-indole 
• 2996-92-1 phenyl trimethylsiloxane 
• 591-50-4 iodobenzene 

Relevant articles and documents

Synthesis of 2-Substituted Benzothio(seleno)phenes and Indoles via Ag-Catalyzed Cyclization/Demethylation of 2-Alkynylthio(seleno)anisoles and 2-Alkynyldimethylanilines

An Ag-catalyzed cyclization/demethylation of 2-alkynylthio(seleno)anisoles and 2-alkynyldimethylanilines is described and applied for the construction of valuable benzothio(seleno)phenes as well as indoles. Various 2-substituted benzothio(seleno)phenes and indoles were obtained in good to excellent yields under mild reaction conditions with low catalyst loading. An application of this new method is also exemplified with a concise synthesis of a bioactive molecule precursor. Furthermore, a conceivable reaction mechanism is proposed with supports from isotope-exchange experiments.

NaNO2/K2S2O8-mediated Selective Radical Nitration/Nitrosation of Indoles: Efficient Approach to 3-Nitro- and 3-Nitrosoindoles

JPZ acknowledges financial support from the National Natural Science Foundation of China (No. 21172163, 21472133), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and Key Laboratory of Organic Synthesis of Jiangsu Province (KJS1749). (Figure presented.).

Direct palladium-catalyzed C-2 and C-3 arylation of indoles: A mechanistic rationale for regioselectivity

We have recently developed palladium-catalyzed methods for direct arylation of indoles (and other azoles) wherein high C-2 selectivity was observed for both free (NH)-indole and (NR)-indole. To provide a rationale for the observed selectivity ("nonelectrophilic" regioselectivity), mechanistic studies were conducted, using the phenylation of 1-methylindole as a model system. The reaction order was determined for iodobenzene (zero order), indole (first order), and the catalyst (first order). These kinetic studies, together with the Hammett plot, provided a strong support for the electrophilic palladation pathway. In addition, the kinetic isotope effect (KIEH/D) was determined for both C-2 and C-3 positions. A surprisingly large value of 1.6 was found for the C-3 position where the substitution does not occur (secondary KIE), while a smaller value of 1.2 was found at C-2 (apparent primary KIE). On the basis of these findings, a mechanistic interpretation is presented that features an electrophilic palladation of indole, accompanied by a 1,2-migration of an intermediate palladium species. This paradigm was used to design new catalytic conditions for the C-3 arylation of indole. In case of free (NH)-indole, regioselectivity of the arylation reaction (C-2 versus C-3) was achieved by the choice of magnesium base.