1891-19-6

Basic information

• Product Name: 1,10-Phenanthroline 1-oxide
• Synonyms: 1,10-Phenanthroline 1-oxide
• CAS NO: 1891-19-6
• Molecular Formula: C₁₂H₈N₂O
• Molecular Weight: 196.2
• Mol File: 1891-19-6.mol
• Article Data: 30

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,10-Phenanthroline 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,10-Phenanthroline 1-oxide(1891-19-6)
• EPA Substance Registry System: 1,10-Phenanthroline 1-oxide(1891-19-6)

Safety Data

• Hazardous Substances Data: 1891-19-6(Hazardous Substances Data)

Usage

General Description

1,10-Phenanthroline 1-oxide is a chemical compound with the molecular formula C12H8N2O. It is a heterocyclic molecule that consists of a phenanthroline ring system with an oxygen atom attached to one of the carbon atoms. 1,10-Phenanthroline 1-oxide is a versatile chemical compound used in various fields such as coordination chemistry, organic synthesis, and biological research. It is known for its ability to chelate metal ions, particularly transition metal ions, and form stable complexes. These complexes have been studied for their potential applications in catalysis, sensing, and medicinal chemistry. Additionally, 1,10-Phenanthroline 1-oxide has been investigated for its potential biological activities and has shown promising results in antitumor and antimicrobial activities.

Upstream product

• 66-71-7 1,10-Phenanthroline 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 

Downstream Products

• 177856-84-7 (1,10-phenanthroline-N-oxide)tris(1-phenyl-4,4,4-trifluorobutane-1,3-dionato)europium(III) 
• 57154-80-0 1,10-phenanthroline-2-carboxylic acid chloride 
• 1891-17-4 1,10-phenanthroline-2-carboxylic acid 
• 22426-17-1 2-phenoxy-1,10-phenanthroline 
• 92695-50-6 1H-[1,10]phenanthrolin-2-one 

Relevant articles and documents

A Fluorine-18 Radiolabeling Method Enabled by Rhenium(I) Complexation Circumvents the Requirement of Anhydrous Conditions

Azeotropic distillation is typically required to achieve fluorine-18 radiolabeling during the production of positron emission tomography (PET) imaging agents. However, this time-consuming process also limits fluorine-18 incorporation, due to radioactive decay of the isotope and its adsorption to the drying vessel. In addressing these limitations, the fluorine-18 radiolabeling of one model rhenium(I) complex is reported here, which is significantly improved under conditions that do not require azeotropic drying. This work could open a route towards the investigation of a simplified metal-mediated late-stage radiofluorination method, which would expand upon the accessibility of new PET and PET-optical probes.

1-Methyl-1,10-phenanthrolin-2(1H)-one (L) as a ligand to Eu(III): Crystal structure and luminescent properties of [Eu(L)3(NO3) 3] Dedicated to Professor George Christou on the occasion of his 60th birthday.

A new coordination compound of Eu(III) with 1-methyl-1,10-phenanthroline- 2(1H)-one (L) as a ligand has been synthesized and characterized using infrared spectroscopy, elemental analysis and single crystal X-ray diffraction. The structure contains isolated [Eu(L)3(NO3)3] molecules interacting through extensive π-stacking. Photoluminescence studies demonstrate that the complex shows line-like emission characteristic of Eu(III) when excited in the ligand-centered absorption bands, with a quantum yield of 22% and a lifetime of 0.74 ms.

From Pyridine- N-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy

The reactions of pyridine-N-oxides with Ph3P under the developed conditions provide an unprecedented route to (pyridine-2-yl)phosphonium salts. Upon activation with DABCO, these salts readily serve as functionalized 2-pyridyl nucleophile equivalents. This umpolung strategy allows for the selective C2 functionalization of the pyridine ring with electrophiles, avoiding the generation and use of unstable organometallic reagents. The protocol operates at ambient temperature and tolerates sensitive functional groups, enabling the synthesis of otherwise challenging compounds.

Reaction of Pyridine-N-Oxides with Tertiary sp2-N-Nucleophiles: An Efficient Synthesis of Precursors for N-(Pyrid-2-yl)-Substituted N-Heterocyclic Carbenes

N-(Pyrid-2-yl)-substituted azolium and pyridinium salts, precursors for hybrid NHC-containing ligands, were obtained with excellent regioselectivity, employing a deoxygenative CH-functionalization of pyridine-N-oxides with substituted imidazoles, thiazoles, and pyridine. Unlike the traditional SNAr-based methods, this approach provides high yields for substrates bearing substituents of different electronic nature. The utility of azolium and pyridinium salts thus prepared was also highlighted by the synthesis of pyridyl-substituted imidazolyl-2-thione, benzodiazepine as well as 2-aminopyridines.