5465-85-0

Basic information

• Product Name: 1-(naphthalen-2-yl)piperidine
• CAS NO: 5465-85-0
• Molecular Formula: C₁₅H₁₇N
• Molecular Weight: 211.3022
• Mol File: 5465-85-0.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 362.9°C at 760 mmHg
• Flash Point: 156.2°C
• Density: 1.079g/cm³
• Vapor Pressure: 1.88E-05mmHg at 25°C
• Refractive Index: 1.621
• CAS DataBase Reference: 1-(naphthalen-2-yl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(naphthalen-2-yl)piperidine(5465-85-0)
• EPA Substance Registry System: 1-(naphthalen-2-yl)piperidine(5465-85-0)

Safety Data

• Hazardous Substances Data: 5465-85-0(Hazardous Substances Data)

Usage

General Description

1-(naphthalen-2-yl)piperidine, also known as 2-Napthylpiperidine, is a chemical compound with the molecular formula C16H17N. It is a piperidine derivative that contains a naphthalene ring attached to the piperidine ring. 1-(naphthalen-2-yl)piperidine is used in the synthesis of various pharmaceuticals and research chemicals, particularly those related to neurological and psychiatric disorders. It has also been studied for its potential as a precursor in the production of opioids and other psychoactive substances. 1-(naphthalen-2-yl)piperidine is known to have psychoactive effects and is classified as a controlled substance in some jurisdictions due to its potential for abuse and dependence.

Upstream product

• 110-89-4 piperidine 
• 580-13-2 2-bromonaphthalene 
• 321-38-0 1-Fluoronaphthalene 
• 60-29-7 diethyl ether 
• 591-51-5 phenyllithium 
• 323-09-1 2-fluoronaphthalene 
• 91-58-7 2-chloronaphthalene 
• 612-55-5 2-iodonaphthalene 
• 90-11-9 1-Bromonaphthalene 
• 90-14-2 1-Iodonaphthalene 
• 90-13-1 1-Chloronaphthalene 
• 135-19-3 β-naphthol 
• 111-24-0 1,5-dibromo-pentane 
• 91-59-8 naphthalen-2-ylamine 

Downstream Products

• 91-20-3 naphthalene 

Relevant articles and documents

-

-

-

-

Mechanistic Insights into the FeCl3-Catalyzed Oxidative Cross-Coupling of Phenols with 2-Aminonaphthalenes

The selective FeCl3-catalyzed oxidative cross-coupling reaction between phenols and primary, secondary, and tertiary 2-aminonaphthalene derivatives was investigated. The generality of this scalable method provides a sustainable alternative for preparing N,O-biaryl compounds that are widely used as ligands and catalysts. Based on a comprehensive kinetic investigation, a catalytic cycle involving a ternary complex that binds to both the coupling partners and the oxidant during the key oxidative coupling step is postulated. Furthermore, the studies showed that the reaction is regulated by off-cycle acid-base and ligand exchange processes.

Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex

Palladium catalyzed visible-light-mediated borylation of inactivated aryl and alkyl halides is reported; the method provided high yields and excellent functional group compatibility. Furthermore, arylsilicates were synthesized selectively using dimethylphenylsilyl boronic ester via changing the reaction conditions. Finally, the possible reaction mechanism is determined through fluorescence quenching and turn on/off experiments.

Redox-neutral: Ortho -C-H amination of pinacol arylborates via palladium(ii)/norbornene catalysis for aniline synthesis

A palladium(ii)/norbornene cooperative catalysis enabled redox-neutral ortho-C-H amination of pinacol aryl- or heteroarylborates for the synthesis of structurally diverse anilines is reported. This method is scalable, robust (tolerance of air and moisture), phosphine ligand-free, and compatible with a wide range of functionalities. These practical features make this reaction amenable for industry. A plethora of synthetically very useful halogenated anilines, which often cannot be prepared via other transition-metal-catalyzed aminations, are readily produced using this method. Particularly, the orthogonal reactivity between pinacol arylborates and aryl iodides is demonstrated. Preliminary deuterium-labeling studies reveal a redox-neutral ipso-protonation mechanism of this process, which will surely inspire the future development of this field. Overall, the exceptionally broad scope (47 examples) and reliability of this procedure, together with the wide availability of pinacol arylborates, make this chemistry a valuable addition to the existing methods for aniline synthesis.