25556-16-5

Basic information

• Product Name: Piperidine, 1,1'-(1,4-phenylene)bis-
• CAS NO: 25556-16-5
• Molecular Formula: C16H24N2
• Molecular Weight: 244.38
• Mol File: 25556-16-5.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Piperidine, 1,1'-(1,4-phenylene)bis-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperidine, 1,1'-(1,4-phenylene)bis-(25556-16-5)
• EPA Substance Registry System: Piperidine, 1,1'-(1,4-phenylene)bis-(25556-16-5)

Safety Data

• Hazardous Substances Data: 25556-16-5(Hazardous Substances Data)

Upstream product

• 110-89-4 piperidine 
• 106-37-6 1.4-dibromobenzene 
• 106-46-7 para-dichlorobenzene 
• 15368-96-4 2,3,5,6-tetrafluoro-1,4-bis(piperidin-1-yl)benzene 
• 2359-60-6 4-(1-piperidino)aniline 
• 111-29-5 1 ,5-pentanediol 
• 150-76-5 4-methoxy-phenol 
• 108-94-1 cyclohexanone 
• 111-24-0 1,5-dibromo-pentane 
• 106-50-3 1,4-phenylenediamine 
• 132647-27-9 1,4-dipiperidino-cyclohexa-1,3-diene 
• 71-43-2 benzene 

Downstream Products

• 1166111-35-8 (E,E)-2,5-bis[2-(ethoxycarbonyl)ethenyl]-1,4-dipiperidinobenzene 

Relevant articles and documents

Preparation of functionalized p-phenylenediamine derivatives using arene-iron chemistry

Selective displacement of chloride from cyclopentadienyl(1,4-dichlorobenzene)iron(1+) by a series of cyclic secondary amine nucleophiles is described. This selectivity, in combination with further manipulation of the complexes, allows access to a series of unsymmetrical and/or functionalized etraalkyl-p-phenylenediamine complexes. A series of demetalated phenylenediamines were shown by CV to have redox potentials distributed over a range of 320 mV, as a consequence of remote functionality. Preliminary fluorescence studies on a series of electron acceptor-substituted phenylenediamines indicated quenching of the phenylenediamine fluorescence, attributable to rapid electron transfer.

Catalytic Amination of Phenols with Amines

Given the wide prevalence and ready availability of both phenols and amines, aniline synthesis through direct coupling between these starting materials would be extremely attractive. Herein, we describe a rhodium-catalyzed amination of phenols, which provides concise access to diverse anilines, with water as the sole byproduct. The arenophilic rhodium catalyst facilitates the inherently difficult keto–enol tautomerization of phenols by means of π-coordination, allowing for the subsequent dehydrative condensation with amines. We demonstrate the generality of this redox-neutral catalysis by carrying out reactions of a large array of phenols with various electronic properties and a wide variety of primary and secondary amines. Several examples of late-stage functionalization of structurally complex bioactive molecules, including pharmaceuticals, further illustrate the potential broad utility of the method.

Synthesis and structural characterization of palladium(II) thiosemicarbazone complex: Application to the Buchwald-Hartwig amination reaction

A simple route to synthesize mononuclear palladium(II) thiosemicarbazone complex has been described. Elemental analysis, spectral methods and single crystal X-ray diffraction analysis were used to confirm the composition of the complex. The new complex acts as an active homogeneous catalyst for the Buchwald-Hartwig amination reaction of a wide range of aryl and heteroaryl halides (bromides and chlorides), including activating, neutral and deactivating substrates, with various secondary amines under optimized conditions.

A new route to polykis(dialkylamino)benzenes and -naphthalenes based on protodefluorination of electron-rich fluoroaromatics: Anion radicals of arenes as a simple and effective alternative to 'classical' LAH-based systems

A simple and effective procedure for protodefluorination of electron-rich fluoroaromatic compounds has been developed. It operates with aromatic anion radicals as reducing agents and shows superior results over 'classical' lithium aluminum hydride based s