78831-36-4

Usage

Uses

Used in Analytical Chemistry:
(1,10-Phenanthroline-2,9-diyl)diMethanol is used as a reagent for the spectrophotometric determination of copper. It forms a colored complex with copper ions, which allows for the quantitative analysis of copper concentrations in various samples.
Used in Biochemistry:
(1,10-Phenanthroline-2,9-diyl)diMethanol is used in the preparation of copper complexes for catalytic and biological studies. Its high affinity for copper ions makes it a useful ligand for the synthesis of copper-containing compounds, which can be further explored for their potential applications in catalysis, medicine, and other fields.
Used in Research:
(1,10-Phenanthroline-2,9-diyl)diMethanol is used as a research tool for studying copper-containing systems. Its unique chemical properties enable the manipulation and investigation of copper ions in various biological and chemical processes, contributing to a better understanding of their roles and interactions in different systems.
Note: The chemical name "Bathocuproine" comes from the term bathophenanthroline, which is derived from phenanthroline, and "cu" represents the symbol for the chemical element copper.

InChI:InChI=1/C14H12N2O2/c17-7-11-5-3-9-1-2-10-4-6-12(8-18)16-14(10)13(9)15-11/h1-6,17-18H,7-8H2

Upstream product

• 57709-61-2 1,10-phenanthroline-2,9-dicarboxylic acid 
• 484-11-7 2.9-dimethyl-1,10-phenanthroline 
• 516462-64-9 bis(pentafluorophenyl)-1,10-phenanthroline-2,9-dicarboxylate 
• 57709-62-3 1,10-phenanthroline-2,9-dicarboxaldehyde 

Downstream Products

• 87518-61-4 2,9-bis-(chloromethyl)-1,10-phenanthroline 
• 1233940-16-3 2,9-bis[(tert-butyldiphenylsilyloxy)methyl]-1,10-phenanthroline 
• 180784-55-8 Benzyl-[9-(benzyl-ethoxy-phosphinoylmethyl)-[1,10]phenanthrolin-2-ylmethyl]-phosphinic acid ethyl ester 

Relevant academic research and scientific papers

Lithium halide ion-pair recognition with halogen bonding and chalcogen bonding heteroditopic macrocycles

A series of halogen bonding and chalcogen bonding phenanthroline containing heteroditopic macrocyclic receptors exhibit cooperative recognition of lithium halide (LiX) ion-pairs. Quantitative 1H NMR ion-pair titration experiments in CDCl3?:?CD3CN (1?:?1,

A new tetradentate mixed aza-thioether macrocycle and its complexation behavior towards Fe(II), Ni(II) and Cu(II) ions

A new tetradentate mixed aza-thioether macrocyclic ligand 2,6-dithia[7](2,9)-1,10-phenanthrolinophane ([13]ane(phenN2)S2) was successfully synthesized. Reacting metal precursors [Fe(CH3CN)2(OTf)2], Ni(ClO4)2·6H2O, and Cu(ClO4)2·6H2O with one equivalent of [13]ane(phenN2)S2 afforded [Fe([13]ane(phenN2)S2)(OTf)2] (1), [Ni([13]ane(phenN2)S2)](ClO4)2 (2(ClO4)2), and [Cu([13]ane(phenN2)S2)(OH2)](ClO4)2 (3(ClO4)2), respectively. The structures of [13]ane(phenN2)S2 and all of its metal complexes were investigated by X-ray crystallography. The [13]ane(phenN2)S2 was found to behave as a tetradentate ligand via its donor atoms N and S.

Re(i) derivatives functionalised with thioether crowns containing the 1,10-phenanthroline subunit as a new class of chemosensors

A series of luminescent fac-[Re(CO)3(L)(NN)]+ complexes, where L is a pyridine or an imidazole and NN is the 1,10-phenanthroline subunit of mixed donor pentadentate thioether crowns have been synthesised and their luminescence properties have been analysed. Then, heterometallic Re(i)/Au(i) complexes, with the Au(i) fragment bonded directly to the imidazole ligand, and heterometallic Re(i)/Ag(i) complexes, with the silver fragment coordinating the S-donor thioether linker of the rings have also been prepared. Analysis of their luminescence properties showed a considerable blue shift of the emission maxima for the Re(i)/Ag(i) derivatives, upon coordination of the silver centre to the S-donor atoms of the aliphatic chain of the macrocyclic units.

Synthesis and DNA-binding properties of 1,10-phenanthroline analogues as intercalating-crosslinkers

(Chemical Equation Presented) We synthesized a series of bis(bromomethyl)4 ,10-phenanthrolines as novel anticancer lead compounds and examined their DNA-binding properties. 5,6-Bis(bromomethyl)-1,10-phenanthroline showed DNA intercalating activity and DNA crosslinking activity, furthermore it is stable in aqueous solution.

Synthesis and characterization of new binaphthyl-linked phenanthroline-, bipyridine-, or pyridine-derived ligands, and the study of their cytotoxic activity

In the present work, we describe the synthesis and characterization of five new versatile acyclic or macrocyclic ligands containing binaphthyl-linked pyridine, bipyridine, or phenanthroline groups in their framework (see Schemes 1-4). The structures of the ligands were elucidated on the basis of elemental analyses, IR, 1H-NMR, 13C-NMR, and FAB mass spectra. The cytotoxicity of these compounds was tested in vitro by using the tetrazolium salt reduction (MTT) assay on A549 (human lung carcinoma epithelial like) cells. All of the tested compounds induced time- and concentration-dependent cytotoxic effect.

Design and synthesis of a neutral fluorescent macrocyclic receptor for the recognition of urea in chloroform

(Chemical Equation Presented) An artificial macrocyclic fluorescent receptor 1 has been designed and synthesized for the recognition of urea. 1 shows significant fluorescence quenching on complexation with urea and thiourea in chloroform and thus may be used as a synthetic fluorescent molecular sensor for their determination in a nondegradative way.

Production method of a cross-coupling compound from an alkyl halide and an organoboron compound

There is provided a method for producing a coupling compound of formula (1):(Y-)(n-1)R1-R2-(R1)(n'-1) wherein R1, R2 n and n' are as defined below, Y is R2 or X as defined below, which method comprises reactinganorganichalogen compound of formula (2):n' (R1X1n) wherein X1 represents a bromine or iodine, R1 represents a substituted or unsubstituted, linear, branched or cyclic hydrocarbon group of which α and β carbon atoms in relation to X1 are sp3 carbon atoms, n and n' each independently represent an integer of 1 or 2, and provided that n and n' do not simultaneously represent 2, with an organic boron compound of formula (3):m{R2(BX22)n'} wherein R2 represents a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted alkenyl group and the boron atom is bonded with an sp2 carbon atom thereof, X2 represents a hydroxyl or alkoxy group, n' is as defined above, m represents an integer of 1 or 2, and m is not more than n, in the presence of a catalyst comprising a) a nickel compound, and ???b) b-1) a compound of formula (i): ???or ???b-2) a compound of formula (ii):

Synthesis of triple helix forming oligonucleotides with a phenanthroline moiety into the 3′-3′ inversion site of polarity

A protocol for the synthesis of triplex forming oligonucleotides containing a chelating molecule in the 3′-3′ inversion site of polarity is reported. A number of 16-mers have been synthesized and UV spectroscopy employed to evaluate the stability of their triple helix complexes with the pertinent double-strand oligonucleotide targets. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002.

Novel phenanthroline-containing trinuclear double-stranded helicates: Self-recognition between helicates with phenanthroline and bipyridine binding sites

The ligands 6,6'-bis[(2-methyl-1,10-phenanthrolin-9- yl)methylenoxymethylenyl] 2,2'-bipyridine (1)- and 2,9-bis[(2-methyl-1,10- phenanthrolin-9-yl)methylenoxymethylenyl] -1,10-phenanthroline (2) were prepared and shown to self-assemble into double-stranded [(L)2Cu3]3+-type helicates upon reaction with Cu+. Although the reaction of 1 with AgCF3SO3 afforded the double-stranded helicate [(1)2Ag3]3+, reaction of 2 with this salt yielded a mixture of several complexes, all of apparently double- strand nature, based on their diffusion coefficients. Addition of a large excess of AgCF3SO3 afforded [(2)2Ag3]3+ as the sole product. In addition, it was found that the reaction of Cu+ with mixtures of 1 and 6''6'''-bis[(6-methyl-2,2'-bipyridin-6'-yl)methylenoxymethylenyl]-2''2'''- bipyridine (4) or of 2 with 2,9-bis[(6-methyl-2,2-bipyridin-6'- yl)methylenoxymethylenyl]-1,10-phenanthroline (3) afforded mixtures of homoleptic and heteroleptic helicates. Helicate distribution seems to follow statistical expectations. Mixing of the double-stranded copper helicates of 2 and 3 in DMSO-d6 afforded, after 2 weeks, a statistical mixture of the homoleptic and heteroleptic helicates, i.e., [(2)2Cu3]3+, [(3)2Cu3]3+, and [(2/3)Cu3]3+. However, a statistical mixture was obtained within minutes from the double-stranded silver helicates of 2 and 3 in CD3CN. We conclude therefore that even 2 and 3, which contain three phenanthroline and three bipyridine binding sites, are not 'sufficiently instructed' to avoid the formation of a heteroleptic helicate in the course of their self-assembly process.

Synthesis of some 2,9-Disubstituted-1,10-phenanthrolines

A series of symmetrically disubstituted compounds, with substituents linked to the ring through a carbon atom, has been prepared from 2,9-dimethyl-1,10-phenanthroline.NMR data are also reported.