6637-11-2

Usage

Indole derivative

A modified version of the parent compound indole.

Methyl groups

Two methyl groups attached at the 1 and 1' positions.

Chemical properties

Not well-studied, but may have potential applications.

Pharmaceutical industry

Possible use in the synthesis of new drugs.

Organic synthesis

May serve as a building block for creating other chemical compounds.

Further research

Necessary to fully understand the properties and potential uses of 2,3'-Bi-1H-indole,2,3-dihydro-1,1'-dimethyl-.

Upstream product

• 603-76-9 1-methylindole 
• 13157-96-5 methyl 2-chloro-2-methoxyacetate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 1415328-91-4 1-methyl-3-[(4-methylphenyl)sulfanyl]-1H-indole 
• 41600-21-9 methyl 2-oxo-2-(pyrrolidin-1-yl)acetate 

Downstream Products

• 1160710-48-4 4-(1-benzyl-1H-indol-3-yl)-4-bis(1-methyl-1H-indol-3-yl)but-3-en-2-one 

Relevant academic research and scientific papers

Switchable regioselection of C-H thiolation of indoles using different TMS counterions

A switchable regioselectivity in C-H thiolation reaction by simply swapping the counteranions of TMS is reported here for the first time. An exclusive C3-H thiolation of indoles with sodium arylsulfinates was achieved in the presence of TMSCl as a promoter. In contrast, with the use of TMSOTf instead of TMSCl under otherwise identical conditions, a regiospecific C2-H thiolation of indoles was realized with the same set of substrates.

Electrooxidation products of methylindoles: Mechanisms and structures

Electrochemical oxidation of 1-methylindole, 2-methylindole and 3- methylindole on a platinum anode in acetonitrile containing NaClO4 has been studied. In any case no polymeric deposit on the working electrode was obtained The identification of the obtained soluble products is described and the mechanisms of formation are discussed. Analogously to the case of unsubstituted indole, electrooxidized 1-3 react through positions 2 and 3. The non polymerization of I is explained with the formation of a tetramer which is oxidized to a stable radical cation and dication without undergoing further coupling reactions.

Vilsmeier Formylation and Glyoxylation Reactions of Nucleophilic Aromatic Compounds Using Pyrophosphoryl Chloride

Reactions of N,N-dimethylformamide and N-methylformanilide with pyrophosphoryl chloride lead to the formation of reagents that undergo reactions with a wide range of nucleophilic aromatic substrates, including indoles, pyrroles, thiophenes, furans, and methoxy-substituted carbocyclic arenes to afford, after hydrolysis of the initial products, good to excellent yields of the expected aldehydes; reactions with methyl oxamates allow the preparation of methyl arylglyoxylates. Key words: pyrophosphoryl chloride, N,N-dimethylformamide, methoxyarene, heterocyle, formylation

Bis-trimethylsilylacetamide: A reagent for the control of Friedel-Crafts alkylation reactions using methyl chloromethoxyacetate

The Friedel-Crafts alkylation reactions of electron rich aromatic compounds using methyl α-chloro-α-methoxyacetate and Lewis acids leads predominantly to the formation of diarylacetic acid derivatives in which the second stage of the sequence is favoured by the presence of hydrogen chloride generated in the first step; effective control can be achieved in a number of cases by the addition of bis-trimethylsilylacetamide.