64943-90-4

Usage

Uses

Used in Psychoactive Substances:
5,6-METHYLENEDIOXY-2-PHENYLINDOLE is used as a psychoactive substance for its ability to induce altered perception, mood enhancement, and sensory distortion. It is often sought after in the context of recreational drug use due to its hallucinogenic properties.
However, it is important to note that the use of 5,6-METHYLENEDIOXY-2-PHENYLINDOLE is associated with potential adverse effects, such as hallucinations, paranoia, and increased heart rate. Due to its potential for abuse and addiction, it is considered illegal in many countries.

InChI:InChI=1/C15H11NO2/c1-2-4-10(5-3-1)12-6-11-7-14-15(18-9-17-14)8-13(11)16-12/h1-8,16H,9H2

Upstream product

• 93-56-1 phenylethane 1,2-diol 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 100-39-0 benzyl bromide 
• 100-42-5 styrene 
• 7748-58-5 1-bromo-4,5-methylenedioxy-2-nitrobenzene 
• 53984-22-8 (E)-5-nitro-6-styrylbenzo[d][1,3]dioxole 

Downstream Products

• 1428443-66-6 2-chloro-1-(6-phenyl-5H-[1,3]dioxolo[4,5-f]indol-7-yl)ethanone 
• 1397586-47-8 (E)-6-phenyl-7-styryl-5H-[1,3]dioxolo[4,5-f]indole 

Relevant academic research and scientific papers

Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates

Alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of 2-nitrostyrenes to give indoles. Whereas the use of alkyl formates requires the presence of a ruthenium catalyst such as Ru3(CO)12, the reaction with phenyl formate can be performed by using a Pd/phenanthroline complex alone. Phenyl formate was found to be the most effective CO source and the desired products were obtained in excellent yields, often higher than those previously reported using pressurized CO. The reaction tolerates many functional groups, including sensitive ones like a free aldehydic group or a pendant pyrrole. Detailed experiments and kinetic studies allow to conclude that the activation of phenyl formate is base-catalyzed and that the metal doesn't play a role in the decarbonylation step. The reactions can be performed in a single thick-walled glass tube with as little as 0.2 mol-% palladium catalyst and even on a 2 g scale. The same protocol can be extended to other nitro compounds, affording different heterocycles.

Pd-Catalyzed Reductive Cyclization of Nitroarenes with CO2 as the CO Source

A reductive amination process that constructs indoles, carbazoles or benzimidazoles from nitroarenes – irrespective of their electronic or steric nature – was developed that uses CO2 as the source of CO. The process is robust, tolerating common gaseous components of flue gas (H2S, SO2, NO and H2O) without adversely affecting the reductive cyclization.

Potassium tert-Butoxide-Promoted Acceptorless Dehydrogenation of N-Heterocycles

Potassium tert-butoxide-promoted acceptorless dehydrogenation of N-heterocycles was efficiently realized for the generation of N-heteroarenes and hydrogen gas under transition-metal-free conditions. In the presence of KOtBu base, a variety of six- and five-membered N-heterocyclic compounds efficiently underwent acceptorless dehydrogenation to afford the corresponding N-heteroarenes and H2 gas in o-xylene at 140 °C. The present protocol provides a convenient route to aromatic nitrogen-containing compounds and H2 gas. (Figure presented.).

Acceptorless Dehydrogenation of N-Heterocycles and Secondary Alcohols by Ru(II)-NNC Complexes Bearing a Pyrazoyl-indolyl-pyridine Ligand

Ruthenium(II) hydride complexes bearing a pyrazolyl-(2-indol-1-yl)-pyridine ligand were synthesized and structurally characterized by NMR analysis and X-ray single crystal crystallographic determinations. These complexes efficiently catalyzed acceptorless dehydrogenation of N-heterocycles and secondary alcohols, respectively, exhibiting highly catalytic activity with a broad substrate scope. The present work has established a strategy to construct highly active transition metal complex catalysts and provides an atom-economical and environmentally benign protocol for the synthesis of aromatic N-heterocyclic compounds and ketones.

Catalytic Synthesis of Substituted Indoles and Quinolines from the Dehydrative C-H Coupling of Arylamines with 1,2- and 1,3-Diols

The cationic ruthenium-hydride complex catalyzes the dehydrative C-H coupling reaction of arylamines with 1,2-diols to form the indole products. The analogous coupling of arylamines with 1,3-diols afforded the substituted quinolines. The catalytic method directly forms these coupling products in a highly regioselective manner without generating any toxic byproducts.

Electrosynthesis of substituted 1H-indoles from o-nitrostyrenes

A novel procedure has been devised for the synthesis of derivatives of 1H-indole that is based on the direct, room-temperature electrochemical reduction of substituted o-nitrostyrenes at carbon cathodes in N,N-dimethylformamide containing tetramethylammonium tetrafluoroborate as supporting electrolyte and in the presence of a 10-fold molar excess of a proton donor (phenol or methyl 3-oxobutanoate).