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:

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

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

Ag(2,2',2''-terpyridyl)(triphenylphosphine)ClO₄

(2,2':6',2''-terpyridyl)aquachlorotriphenyltin(IV)

Refernces

• 1、 Newkome, George R.,Hager, David C.,Fronczek, Frank R.. "Isolation and X-Ray Crystal Structure of a Novel Dihydroterpyridine Dimer formed via an Anionic Cycloaddition". . p. 858 - 859. Retrieved 1981.
• 2、 Adrian Jr., James C.,Hassib, Lamyaa,De Kimpe, Norbert,Keppens, Marian. "A new approach to symmetric 2,2':6',2'-terpyridines". . p. 2365 - 2370. Retrieved 1998.
• 3、 Zhao, Qing-Qing,Ren, Ning,Zhang, Jian-Jun. "Syntheses, crystal structures, luminescence and thermal properties of three lanthanide complexes with 2-bromine-5-methoxybenzoate and 2,2:6′,2″-terpyridine". . p. 1 - 5. Retrieved 2018.
• 4、 Yamamoto, Yutaka,Tanaka, Takuo,Yagi, Masayoshi,Inamoto, Masayuki. "Studies on organometallic compounds. IX. Synthesis of bipyridine N-oxides and terpyridines by palladium catalyzed cross-coupling reaction of trimethylstannylpyridines with bromopyridines". . p. 189 - 194. Retrieved 1996.
• 5、 Pabst, Gunther R.,Sauer, Juergen. "A new and simple 'LEGO' system for the synthesis of 2,6-oligopyridines". . p. 6687 - 6690. Retrieved 1998.
• 6、 Cooke, Michael W.,Wang, Jianhua,Theobald, Isabelle,Hanan, Garry S.. "Convenient one-pot procedures for the synthesis of 2,2′:6′, 2″-terpyridine". . p. 1721 - 1726. Retrieved 2006.
• 7、 Harzmann, Gero D.,Neuburger, Markus,Mayor, Marcel. "4,4″-disubstituted terpyridines and their homoleptic FeII complexes". . p. 3334 - 3347. Retrieved 2013.
• 8、 Lentz, Cédric,Schott, Olivier,Auvray, Thomas,Hanan, Garry S.,Elias, Benjamin. "Design and photophysical studies of iridium(iii)-cobalt(iii) dyads and their application for dihydrogen photo-evolution". supporting information. p. 15567 - 15576. Retrieved 2019/11/03.