2,2':6',2''-Terpyridine

Base Information

• Chemical Name: 2,2':6',2''-Terpyridine
• CAS No.: 1148-79-4
• Molecular Formula: C15H11N3
• Molecular Weight: 233.272
• Hs Code.: 29333990
• European Community (EC) Number: 214-559-5
• NSC Number: 36755,3905
• UNII: G5E357ISH5
• DSSTox Substance ID: DTXSID2061567
• Nikkaji Number: J7.284B
• Wikipedia: Terpyridine
• Wikidata: Q408228
• Metabolomics Workbench ID: 66937
• ChEMBL ID: CHEMBL89445
• Mol file: 1148-79-4.mol

Synonyms:2,2',2''-terpyridine;2,2',2''-terpyridine diperchlorate;2,2',2''-tripyridine

Chemical Property of 2,2':6',2''-Terpyridine

Chemical Property:

• Melting Point: 90-93 °C
• Refractive Index: 1.5610 (estimate)
• Boiling Point: 402.259 °C at 760 mmHg
• PKA: 4.60±0.10(Predicted)
• Flash Point: 182.528 °C
• PSA: 38.67000
• Density: 1.168 g/cm³
• LogP: 3.20560
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: dioxane: 0.1 g/mL, clear
• Water Solubility.: 1.472g/L(24.99 oC)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 233.095297364
• Heavy Atom Count: 18
• Complexity: 232

Purity/Quality:

99% ^*data from raw suppliers

2,2'':6'',2''''-Terpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,T
• Hazard Codes: T+,T
• Statements: 27/28-37/38-41
• Safety Statements: 26-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=NC(=C1)C2=NC(=CC=C2)C3=CC=CC=N3
• Description: A case of occupational dermatitis was reported in a chemical technician, with no cross reactivity to pyridine derivatives.
• Uses: 2,2';6',2"-terpyridine is widely utilized in the field of supramolecular chemistry, which is used to manufacture the racks, ladders and grids, helicates, catenanes and dendrimers. It plays an important role as a ligand in coordination chemistry. Its complexes are employed in the oxidation of alcohols, the carbonylation of aromatic compounds and as oxygen-binding molecules. Functionalized terpyridine ligands were used in semiconductors and solar panels. It forms chealate complexes with europium(III) and terbium(III), which is used in protein labelling.

Technology Process of 2,2':6',2''-Terpyridine

There total 58 articles about 2,2':6',2''-Terpyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.9%

4-pyridylboronic acid (1692-15-5) + 4-bromo-2,2'-bipyridyl (14162-95-9) → 2,2':6,2''-terpyridine (1148-79-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,2-dimethoxyethane; for 96h; Inert atmosphere; Schlenk technique; Reflux;

DOI:10.1039/c9dt01989h

Reference yield: 81.5%

5-bromo-2,2'-bipyridyl (15862-19-8) + 4-pyridylboronic acid (1692-15-5) → 2,2':6,2''-terpyridine (1148-79-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,2-dimethoxyethane; for 96h; Inert atmosphere; Schlenk technique; Reflux;

DOI:10.1039/c9dt01989h

Reference yield: 76.7%

2-acetylpyridine (1122-62-9) + 3-(dimethylamino)-1-(pyridine-2-yl)prop-2-en-1-one (66521-54-8,75415-00-8,123367-25-9) → 2,2':6,2''-terpyridine (1148-79-4)

Guidance literature:

2-acetylpyridine; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 3h; Large scale;

3-(dimethylamino)-1-(pyridine-2-yl)prop-2-en-1-one; In tetrahydrofuran; at 20 ℃; for 18h; Large scale;

With ammonium acetate; acetic acid; In tetrahydrofuran; for 5h; Reflux; Large scale;

upstream raw materials:

pyridine

[2,2]bipyridinyl

2-bromo-pyridine

2-bromo-6-(pyridin-2-yl)pyridine

Downstream raw materials:

6-bromo-2,2':6',2''-terpyridine

6,6-dibromo-2,2':6',2-terpyridine

6,6''-diphenyl 2,2',6',2''-terpyridine

2,2',6',2''-terpyridine-1,1',1''-trioxide

Refernces

Unusual nitro-coordination of europium(iii) and terbium(iii) with pyridinyl ligands

10.1039/c2dt31308a

The study investigates a new family of ligands based on picoline, bipyridine, and terpyridine, each containing a nitro moiety, and their coordination and sensitization abilities for lanthanide ions, specifically europium(III) (Eu(III)) and terbium(III) (Tb(III)). The researchers synthesized four ligands: 6-nitro-2,2'-bipyridine (5a), 6'-methyl-6-nitro-2,2'-bipyridine (5b), 6-nitro-2,2';6',2''-terpyridine (5c), and bis(pyridin-2-ylmethyl)(6-nitro-pyridin-2-ylmethyl)amine (6). These ligands were found to coordinate not only through the pyridine nitrogen but also through an oxygen atom of the nitro moiety. The study characterized three new complexes using X-ray single crystal diffraction: 5cTb (a terpyridine-nitro derivative with Tb(NO3)3), its Eu(III) analog 5cEu, and 6Eu (a tripodal amine with a nitro-derivatized pyridine with Eu(CF3SO3)3). All four ligands demonstrated the ability to sensitize Eu(III) and Tb(III) luminescence. The study also explored the photophysical properties of these ligands and their complexes, finding that while the ligands adequately positioned their singlet and triplet states for energy transfer, the process was inefficient, likely due to competing energy transfer pathways involving the nitro group.

Cu(NN)₂Cl₂ and Cu(NNN)Cl₂ and HgCl ₂ building blocks in the synthesis of coordination compoundsX-ray studies and magnetic properties

10.1016/j.jssc.2010.06.015

The research investigates the synthesis and structural characterization of a series of coordination compounds containing Cu(N–N)2Cl2, Cu(N–N–N)Cl2, and HgCl2 building blocks. The purpose of this study is to explore the structural dimensionality and magnetic properties of these compounds, which are synthesized using various ligands such as bis(pyrazol-1-yl)methane (bpzm), bis(3,5-dimethylpyrazol-1-yl)methane (bdmpzm), 2,2-dipyridylamine (dpa), 5,6-diphenyl-3-(2-pyridyl)-1,2,4-trazine (dppt), 2,2'-bipyridine (bipy), and 2,2:6,2'-terpyridine (terpy). The researchers observed an increase in structural dimensionality for compounds [Cu(bpzm)2][HgCl4], [Cu(dpa)2][HgCl3]2, and [Cu(terpy)(m-Cl)HgCl3], and conducted magnetic measurements on complexes [Cu(bpzm)2][HgCl4] and [Cu(terpy)(m-Cl)HgCl3]. The study concludes that the HgCl2 moiety can accept chloride ligands from the Cu(II) centers to form binuclear or polynuclear complexes, and in the case of [Cu(terpy)(m-Cl)HgCl3], there is very weak antiferromagnetic interaction of copper centers in the one-dimensional chain.