57709-62-3

Basic information

• Product Name: [1,10]PHENANTHROLINE-2,9-DICARBALDEHYDE
• Synonyms: [1,10]PHENANTHROLINE-2,9-DICARBALDEHYDE;1,10-phenanthroline-2,9-dicarboxaldehyde;2,9-Diformyl-1,10-phenanthroline;3,8-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline
• CAS NO: 57709-62-3
• Molecular Formula: C₁₄H₈N₂O₂
• Molecular Weight: 236.23
• Product Categories: MOFS COFS
• Mol File: 57709-62-3.mol
• Article Data: 67

Chemical Properties

• Melting Point: 230 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 503.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.410±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 2.12±0.30(Predicted)
• CAS DataBase Reference: [1,10]PHENANTHROLINE-2,9-DICARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: [1,10]PHENANTHROLINE-2,9-DICARBALDEHYDE(57709-62-3)
• EPA Substance Registry System: [1,10]PHENANTHROLINE-2,9-DICARBALDEHYDE(57709-62-3)

Safety Data

• Hazardous Substances Data: 57709-62-3(Hazardous Substances Data)

Usage

General Description

[1,10]PHENANTHROLINE-2,9-DICARBALDEHYDE is a chemical compound with the molecular formula C18H12N2O2. It is a derivative of phenanthroline, which is used as a chelating ligand in coordination chemistry. [1,10]PHENANTHROLINE-2,9-DICARBALDEHYDE is often used in analytical chemistry as a reagent for the determination of various metal ions, such as iron and copper, due to its ability to form stable complexes with these metals. Additionally, [1,10]PHENANTHROLINE-2,9-DICARBALDEHYDE has been studied for its potential biological activities, including its anti-cancer properties and its ability to act as a fluorescent probe for biological molecules. It has also been used in the development of chemical sensors and luminescent materials.

Upstream product

• 57709-61-2 1,10-phenanthroline-2,9-dicarboxylic acid 
• 484-11-7 2.9-dimethyl-1,10-phenanthroline 

Downstream Products

• 826336-54-3 [Cu₂(C₁₂H₆N₂(CHNC₆H₄SO₃)2)2]^(2-) 
• 1227783-56-3 5M₅M-FD 
• 1533454-15-7 N,N’-diethyl-N,N’-ditolyl-2,9-dicarboxamide-1,10-phenanthroline 
• 181063-25-2 [Cu((4-methylphenyl)pyridin-2-ylmethylene-amine)2]⁽¹⁺⁾ 
• 908240-22-2 (C₁₂H₆N₂(CHNC₆H₄CH₃)2)2Cu₂⁽²⁺⁾ 
• 899795-23-4 (C₁₂H₆N₂(CHNC₉H₆N)2)2Cu₃⁽³⁺⁾ 
• 929895-45-4 PhenDC3 
• 478813-38-6 2,9-diformyl-1,10-phenanthrolinebis(2,4,6-trimethylanil) 
• 478813-36-4 2,9-diformyl-1,10-phenanthrolinebis(2,6-dimethylanil) 
• 478813-34-2 2,9-bis[(2,6-diisopropylphenylimino)methyl]phenanthroline 

Relevant articles and documents

Synthesis, characterization, second and third order non-linear optical properties and luminescence properties of 1,10-phenanthroline-2,9-di(carboxaldehyde phenylhydrazone) and its transition metal complexes

The requirement for materials which exhibit good second and third order non-linear optical properties and also for materials which could sense metals in trace quantities has kindled renewed investigations. Organometallics and coordination compounds show a

Potential cytotoxic and amoebicide activity of first row transition metal compounds with 2,9-bis-(2′,5′-diazahexanyl)-1,1-phenanthroline (L1)

A new synthetic pathway was reported to obtain N6 donor ligand 2,9-bis-(2′,5′-diazahexanyl)-1,10-phenanthroline (L1) and its coordination compounds of essential divalent metal ions Mn, Fe, Co, Ni, Cu and Zn. Complete characterization of all compounds was done with the conventional techniques. Crystal structures of [NiL1](PF6)2 and [ZnL1](PF6)2·H2O were also reported. Electrochemical studies have shown an active participation of the aromatic moiety of the ligand in redox reactions. The in vitro tests of the cytotoxic activity against human tumour cell lines HeLa (cervix) and CHP-212 (neuroblastoma) showed that all coordination compounds that involve redox active metal ions exhibit noteworthy antiproliferative activity, superior in all cases to cisplatin. [CuL1]2+ showed the lower IC50 value in the HeLa cell line with 1.84 μM, meanwhile, [CoL1]2+ showed the lower value in neuroblastoma CHP-212 with IC50 = 45.28 μM. None of these compounds were active against the SK-N-SH neuroblastoma cell line. In Entamoeba histolytica cultures, remarkable nanomolar IC50 values were found for [NiL1]2+ and [MnL1]2+ with 60 nM and 80 nM respectively, improving the antiproliferative activity more than 1000 times compared with the first choice drug for clinical treatments of human amoebiasis, metronidazole. On the other hand, a free ligand does not show antiproliferative activity either on human tumor cell lines or on Entamoeba histolytica trophozoites, highlighting the role played by metal ions to produce cytotoxicity in tumor cells and protozoa systems.

1,10-Phenanthroline-based hexacatenar LCs with complex self-assembly, photophysical and binding selectivity behaviors

A novel series of V-shaped phenanthroline-based hexacatenars containing a 1,10-phenanthroline which was substituted on 2,9- positions with two cyanovinyl units were synthesized using oxidation and Knoevenagel reactions. The self-assembly, photophysical pr

A novel O-phenanthroline-based bis(half-salamo)-like chemical sensor: For rapid and efficient continuous recognition of Cu2+, HPO42? and H2PO4?

A novel O-phenanthroline-based bis(half-salamo)-like fluorescent chemical sensor LPOV with two N3O coordination sites was synthesized. These N3O coordination sites were used for binding to specific metal ions. The sensor L

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.

Tritopic phenanthroline and pyridine tail-tied aza-scorpiands

The synthesis of two new tritopic double-scorpiand receptors in which two equivalent 5-(2-aminoethyl)-2,5,8-triaza[9]-(2,6)-pyridinophane moieties have been linked with 2,6-dimethylpyridine (L1) or 2,9-dimethylphenanthroline (L2) units is reported for the

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.

A simple strategy for the visual detection and discrimination of Hg2+and CH3Hg+species using fluorescent nanoaggregates

Fluorescent nanoaggregates (FNAs) based on phenanthroline-based amphiphiles show changes in solution color from colorless to yellow upon addition of both Hg2+(LOD ～4 ppb) and CH3Hg+(LOD ～18 ppb). However, the extent of flu

Synthesis and structural properties of hexaaza[5]helicene containing two [1,2,3]triazolo[1,5-a]pyridine moieties

We have synthesized a novel hexaaza[5]helicene in a straightforward way from neocuproine. The crystal structure has been elucidated with direct-space strategy TALP which demonstrates the power of the powder X-ray diffraction technique. In this crystal structure it is possible to see an interplanar angle of 33(1) between the two triazolopyridine rings. The centrosymmetric crystal structure is a racemic mixture, but the resolution was not possible due to a ring-chain isomerization in a solution that produces a dynamic racemization.

Designer ligands. VII. Synthesis of biomimetic Schiff-base ligands

The preparation of a series of novel acyclic and macrocyclic Schiff-base ligands, designed to model the tyrosinase receptor, is described.

Selective separation of americium from europium using 2,9-bis(triazine)-1,10-phenanthrolines in ionic liquids: a new twist on an old story

Bis-triazine phenanthrolines have shown great promise for f-block metal separations, attributable to their highly preorganized structure, nitrogen donors, and more enhanced covalent bonding with actinides over lanthanides. However, their limited solubility in traditional solvents remains a technological bottleneck. Herein we report our recent work using a simple 2,9-bis(triazine)-1,10-phenanthroline (Me-BTPhen) dissolved in an ionic liquid (IL), demonstrating the efficacy of IL extraction systems for the selective separation of americium from europium, achieving separation factors in excess of 7500 and selectively removing up to 99% of the americium. Characterization of the coordination environment was performed using a combination of X-ray absorption fine structure spectroscopy (XAFS) and density functional theory (DFT) calculations.

Polyoxometalate-Based Frameworks as Adsorbents for Drug of Abuse Extraction from Hair Samples

The linkage of molecular components into functional heterogeneous framework materials has revolutionized modern materials chemistry. Here, we use this principle to design polyoxometalate-based frameworks as high affinity adsorbents for drugs of abuse, leading to their application in solid-phase extraction analysis. The frameworks are assembled by the reaction of a Keggin-type polyanion, [SiW12O40]4-, with lanthanoids Dy(III), La(III), Nd(III), and Sm(III) and the multidentate linking ligand 1,10-phenanthroline-2,9-dicarboxylic acid (H2PDA). Their reaction leads to the formation of crystalline 1D coordination polymers. Because of the charge mismatch between the lanthanoids (+3) and the dodecasilicotungstate (-4), we observe incorporation of the PDA2- ligands into crystalline materials, leading to four polyoxometalate-based frameworks where Keggin-type heteropolyanions are linked by cationic {Lnn(PDA)n} groups (Ln = Dy (1), La (2), Nd (3), and Sm (4)). Structural analysis of the polyoxometalate-based frameworks suggested that they might be suitable for surface binding of common drugs of abuse via supramolecular interactions. To this end, they were used for the extraction and quantitative determination of four model drugs of abuse (amphetamine, methamphetamine, codeine, and morphine) by using micro-solid-phase extraction (D-μSPE) and high-performance liquid chromatography (HPLC). The method showed wide linear ranges, low limits of detection (0.1-0.3 ng mL-1), high precision, and satisfactory spiked recoveries. Our results demonstrate that polyoxometalate-based frameworks are suitable sorbents in D-μSPE for molecules containing amine functionalities. The modular design of these networks could in the future be used to expand and tune their substrate binding behavior.

Synthesis and structural characterization of a novel seven-coordinate cobalt(II) complex: 2,9-Bis(ethanolamine)-1,10-phenanthrolinechlorocobalt(II) chloride

Condensation reaction of 2,9-dicarboxaldehyde-1,10-phenanthroline with 2-aminoethanol followed by NaBH4 reduction yielded the polydentate Schiff base ligand 2,9-bis(ethanolamine)-1,10-phenanthroline in its reduced form. This ligand was characterized by elemental analysis, LC-MS, IR, UV-Vis and NMR spectroscopy. Reaction of the reduced Schiff base ligand with aqueous solution of cobalt(II) chloride affords 2,9-bis(ethanolamine)-1,10- phenanthrolinechlorocobalt(II) chloride in high yield. Single crystals of the cobalt(II) complex were obtained from the crystallization in ethanol and its structure was elucidated by X-ray structural analysis. The cobalt(II) complex ion was found to be seven-coordinated in a pentagonal bipyramidal geometry, whereby cobalt(II) ion is surrounded by the six donor atoms in the ligand molecule and a chloride ion.

Synthesis, structural elucidation, DNA binding, cleavage, AChE and BuChE cholinesterase efficiencies of metal complexes with 1,10-phenanthroline scaffold

A series of metal complexes containing a 1,10-phenanthroline scaffold [ML] (L-1,10-Phenanthroline derivative comprises conjugated aromatic core and electron withdrawing –NO2 group); M = Cu(II), Zn(II), Co(II), and Zn(II) ions were designed and synthesized to obtain effective anti-cholinesterase efficiencies of metal chelates. Analytical and spectroscopic studies were used to determine the structural features. An octahedral structure with moderate distortion was attributed to the above metal chelates based on spectroscopic data. S. aureus, A. niger, C. albicans, B.subtilis, A. flavus, and E. coli were used to test the antibacterial efficacy of the synthesized ligands and metal complexes. Using agarose gel electrophoresis, the DNA fragmentation proficiency of prepared metal complexes was tested on pUC 18 DNA. The distorted octahedral geometry of the copper(II) complex to DNA (K b = 4.11 × 105 M?1) is stronger than that of ethidium bromide (EB) to DNA (K b = 3.3 × 105 M?1) and other metal complexes, respectively. The synthesized 1,10-phenanthroline derivative had the best inhibitory effects against acetylcholinesterase and butyrylcholinesterase, with IC50 values of 0.45 and 3.6 M, respectively, which were lower than the reference molecules. Our experimental results may contribute to the development of new drug molecules particularly in the treatment of neurological disorders including glaucoma, Alzheimer’s disease and diabetes. The actions of inhibitors on the glycosidase enzyme help to delay the breakdown and release of sugar molecules into the bloodstream, and they can be used as therapeutic factors in the treatment of diabetes.

New 2,9-disubstituted-1,10-phenanthroline derivatives with anticancer activity by selective targeting of telomeric G-quadruplex DNA

Fifteen new 1,10-phenanthrolines disubstituted at positions 2 and 9 via amide bonds with different heterocycles have been designed and synthesized as G-quadruplex DNA stabilizers. Ten compounds were evaluated for the in vitro anticancer activity against 60 human tumor cell lines panel, four of them showing a very good inhibitory activity on several cell lines. To assess the ability of the most active compounds to interact with G-quadruplex DNA (G4-DNA), circular dichroism experiments were performed. The potency of the compounds to stabilize the G4-DNA has been shown from the thermal denaturation experiments. The mechanism of compounds binding to DNA and to G4-DNA was theoretically investigated by molecular docking studies. The experimental results demonstrated excellent capacity of the two compounds bearing two pyridin-3-yl residues (methylated and non-methylated) to act as selective G-quadruplex binders with promising anticancer activity.