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| Product Name: | 2,2':6',2''-TERPYRIDINE | | Synonyms: | 2,2':6',2''-Terpyridine,97%;2,2′:6′,2′′-Terpyridine ,98%;6',2'']Terpyridine;2,2',2" TERPYRIDINE (Tripyridine, Tripyridyl);´;2,2':6',2"-Terpyridine 98%;2,6-BIS(PYRIDIN-2-YL)PYRIDINE;TERPY | | CAS: | 1148-79-4 | | MF: | C15H11N3 | | MW: | 233.27 | | EINECS: | 214-559-5 | | Product Categories: | Pyrimidines;Achiral Nitrogen;Py-N | | Mol File: | 1148-79-4.mol |  |
| | 2,2':6',2''-TERPYRIDINE Chemical Properties |
| Melting point | 90-93 °C | | Boiling point | 370 °C | | density | 1.1901 (rough estimate) | | refractive index | 1.5610 (estimate) | | storage temp. | Sealed in dry,Room Temperature | | solubility | dioxane: 0.1 g/mL, clear | | form | Crystalline powder | | pka | 4.60±0.10(Predicted) | | color | Cream to yellow to brown | | Water Solubility | 1.472g/L(24.99 ºC) | | BRN | 11199 | | InChIKey | DRGAZIDRYFYHIJ-UHFFFAOYSA-N | | CAS DataBase Reference | 1148-79-4(CAS DataBase Reference) | | EPA Substance Registry System | 2,2':6',2''-Terpyridine (1148-79-4) |
| | 2,2':6',2''-TERPYRIDINE Usage And Synthesis |
| Application in coordination chemistry | As an NNN-tridentate ligand, the 2,2′:6′,2″-terpyridine plays an important role in coordination chemistry. With three coordination sites and low LUMO, terpyridine and its derivatives are one of the typical Pincer ligand and/or non-innocent ligands in transition metal catalysis. Interesting catalytic reactivities have been obtained with these tpy-metal complexes targeting some challenging transformations, such as C–C bond formation and hydrofunctionalization. The 2,2':6':2''-terpyridine ligand has literally shaped the coordination chemistry of transition metal complexes in a plethora of fields.
| | Description | A case of occupational dermatitis was reported in a
chemical technician, with no cross reactivity to pyridine
derivatives. | | Chemical Properties | Off-white crystal | | 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. | | Definition | ChEBI: A tridentate heterocyclic ligand that binds metals at three meridional sites giving two adjacent 5-membered MN2C2 chelate rings. | | Synthesis Reference(s) | Journal of the American Chemical Society, 103, p. 3585, 1981 DOI: 10.1021/ja00402a062
Organic Syntheses, Coll. Vol. 7, p. 476, 1990 | | General Description | 2,2′:6′,2′′;-Terpyridine is a tridentate ligand that can be prepared in two steps starting from 2-acetylpyridine. | | Contact allergens | This molecule is a terpyridine with a 4-methyl substitution. A case of occupational dermatitis was reported in a chemical technician with no cross-reactivity to pyridine derivatives. | | Purification Methods | Crystallise it from diethyl ether, toluene or from pet ether, then aqueous MeOH, followed by sublimation in a vacuum at 90o. It is used for estimating Ag and Ru. [Kamra et al. Anal Chim Acta 81 177 1976, Beilstein 26 III/IV 258.] |
| | 2,2':6',2''-TERPYRIDINE Preparation Products And Raw materials |
| Raw materials | 3,3-bis(methylsulfanyl)-1-pyridin-2-ylprop-2-en-1-one-->TRIMETHYL(2-PYRIDYL)TIN-->2,6-Diiodopyridine-->4'-(METHYLTHIO)-2,2':6',2''-TERPYRIDINE-->4-Bromo-2,2''-bipyridine-->4'-CHLORO-2,2':6',2''-TERPYRIDINE-->5-BROMO-2,2'-BIPYRIDINE-->6-BROMO-2,2'-BIPYRIDINE-->2-Acetylpyridine-->2,6-Dibromopyridine-->Pyridine-4-boronic acid |
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