89333-97-1

Basic information

• Product Name: 1,10-Phenanthroline, 2,9-bis(4-methoxyphenyl)-
• CAS NO: 89333-97-1
• Molecular Formula: C26H20N2O2
• Molecular Weight: 392.457
• Mol File: 89333-97-1.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: 1,10-Phenanthroline, 2,9-bis(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,10-Phenanthroline, 2,9-bis(4-methoxyphenyl)-(89333-97-1)
• EPA Substance Registry System: 1,10-Phenanthroline, 2,9-bis(4-methoxyphenyl)-(89333-97-1)

Safety Data

• Hazardous Substances Data: 89333-97-1(Hazardous Substances Data)

Usage

General Description

1,10-Phenanthroline, 2,9-bis(4-methoxyphenyl)- is a type of organic compound that belongs to the family of phenanthroline derivatives. It is a complexing agent that can form stable complexes with various metal ions, particularly with transition metals such as copper, iron, and ruthenium. 1,10-Phenanthroline, 2,9-bis(4-methoxyphenyl)- is commonly used in analytical chemistry and biochemistry as a chelating agent to isolate and quantify metal ions in solution. Additionally, it has potential applications in the field of coordination chemistry, catalysis, and material science due to its ability to modulate the properties of metal complexes and materials. The presence of methoxy groups in its chemical structure can also impart specific properties and reactivity to the compound.

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 66-71-7 1,10-Phenanthroline 
• 95246-98-3 {Cu(I)(2,9-di-p-anisyl-1,10-phenanthroline)2}BF₄*H₂O 
• 121705-02-0 {Cu(II)(2,9-di-p-anisyl-1,10-phenanthroline)2}⁽²⁺⁾ 
• 121730-26-5 {Cd(II)(2,9-di-p-anisyl-1,10-phenanthroline)2}⁽²⁺⁾ 
• 39588-59-5 3,6,7,9-tetrahydro-5H-<1,4>diazepino<1,2,3,4-lmn><1,10>phenanthroline-3,9-dione 
• 15302-99-5 6,7-dihydro-5H-[1,4]diazepino[1,2,3,4-l,m,n][1,10]phenanthroline-4,8-diium dibromide 
• 5144-89-8 1,10-phenanthroline hydrate 
• 14774-77-7 p-methoxyphenyllithium 
• 5720-07-0 4-methoxyphenylboronic acid 
• 29176-55-4 2,9-dichloro-[1,10]phenanthroline 

Downstream Products

• 121705-02-0 {Cu(II)(2,9-di-p-anisyl-1,10-phenanthroline)2}⁽²⁺⁾ 
• 121704-89-0 {Co(II)(2,9-di-p-anisyl-1,10-phenanthroline)2}(ClO₄)2 
• 121704-84-5 Ag(dap)2⁽¹⁺⁾ 
• 95246-99-4 [Cu(2,9-di(p-anisyl)-1,10-phenanthroline)2]BF₄ 
• 95246-98-3 {Cu(I)(2,9-di-p-anisyl-1,10-phenanthroline)2}BF₄*H₂O 
• 121730-26-5 Zn(dap)2⁽²⁺⁾ 
• 95246-98-3 Cu(2,9-di(p-anisyl)-1,10-phenanthroline)2⁽¹⁺⁾ 
• 121730-26-5 {Cd(II)(2,9-di-p-anisyl-1,10-phenanthroline)2}⁽²⁺⁾ 
• 121704-84-5 {Ag(I)(2,9-di-p-anisyl-1,10-phenanthroline)2}BF₄ 
• 1208256-38-5 [Cu((CH₃)2C₅₁H₄₂N₂O₄)(2,9-dianisylphenanthroline)]PF₆ 
• 1395348-64-7 (2-[4-(trityloxy)phenyl]-9-[4-(2-cyanoethyldiisopropylphosphoramidyl)phenyl]-1,10-phenanthroline) 
• 1395348-65-8 2-[4-(trityloxy)phenyl]-9-[4-(hydroxyphenyl)]-1,10-phenanthroline 

Relevant articles and documents

Cu-tethered macrocycle catalysts: Synthesis and size-selective CO2-fixation to propargylamines under ambient conditions

A novel air-stable, Cu-tethered macrocycle catalyst possessing a large inner cavity was successfully synthesized, creating a unique supramolecular catalytic system. The catalyst was utilized in the CO2-fixation reaction to propargylamines. The reaction proceeded more efficiently compared to the conventional CuI catalyst under atmospheric CO2 condition. Notably, owing to its topological effect, the Cu-tethered macrocycle catalyst exhibited unique substrate size selectivity.

One-Pot Synthesis of a Linear [4]Catenate Using Orthogonal Metal Templation and Ring-Closing Metathesis

The efficient synthesis of well-defined, linear oligocatenanes possessing multiple mechanical bonds remains a formidable challenge in the field of mechanically interlocked molecules. Here, a one-pot synthetic strategy is described to prepare a linear [4]catenate using orthogonal metal templation between a macrocycle precursor, composed of terpyridine and phenanthroline ligands spaced by flexible glycol linkers, and a closed phenanthroline-based molecular ring. Implementation of two simultaneous ring-closing metathesis reactions after metal complexation resulted in the formation of three mechanical bonds. The linear [4]catenate product was isolated in 55% yield as a mixture of topological diastereomers. The intermediate metal complexes and corresponding interlocked products (with and without metals) were characterized by nuclear magnetic resonance, mass spectrometry, gel permeation chromatography, and UV-vis absorption spectroscopy. We envision that this general synthetic strategy may pave the way for the synthesis of higher order linear oligocatenates/catenanes with precise molecular weights and four or more interlocking molecular rings.

Supramolecular polymerization of a ureidopyrimidinone-based [2]catenane prepared via ring-closing metathesis

The synthesis of a Sauvage-type [2]catenane featuring a quadruple hydrogen bonding ureidopyrimidinone (UPy) motif in each ring was reported. Intermolecular dimerization of the UPy motifs induces the hydrogen-bond-driven supramolecular polymerization of the [2]catenane monomer, thereby creating a linear polymer consisting of both hydrogen bonding and mechanical bonds. As the rings in the UPy catenane are asymmetric, two stereoisomers can be formed upon catenation, that is, with the phenanthroline moieties oriented +90° or -90° with respect to each other. Based on the phenanthroline-Cu(I) and ring-closing metathesis (RCM) approach, we first devised a synthetic procedure for the synthesis of the UPy-based catenane. Here, phenanthroline was first functionalized with phenol moieties in a two-step approach with an overall yield of 46%. The resulting biphenol 3 was then alkylated in a statistical manner with a mixture of 4-bromobut-1-ene and t-Boc-protected bromide resulting in t-Boc-protected compound. The results show that protection of the UPy motifs is necessary for this reaction to reach completion. Analysis of the unprotected UPy catenane by 1H NMR revealed the formation of UPy-UPy dimers and significant broadening of the signals, both in presence and absence of Cu(I).