| Identification | More | [Name]
2,2':6',2''-TERPYRIDINE | [CAS]
1148-79-4 | [Synonyms]
2,2',2''-TERPYRIDINE
2,2',2''-TRIPYRIDINE
2,2',2''-TRIPYRIDYL
2,2':6',2''-TERPYRIDINE
2->2',6'->2''-TERPYRIDINE
2,6-BIS(2-PYRIDYL)PYRIDINE
2,6-DI(2-PYRIDYL)PYRIDINE
ALPHA,ALPHA',ALPHA''-TERPYRIDINE
ALPHA,ALPHA',ALPHA''-TRIPYRIDYL
TERPY
TIMTEC-BB SBB008932
TRIPYRIDINE
TRIPYRIDYL
2,2',2''-Terpyridyl
Ba 2799
Terpyridine
TerpyridineminTERPYoffwhitepowder
2,2',2-TripyridylA.R.
2,2':6',2'-Terpyridino
Terpyridyl | [EINECS(EC#)]
214-559-5 | [Molecular Formula]
C15H11N3 | [MDL Number]
MFCD00006213 | [Molecular Weight]
233.27 | [MOL File]
1148-79-4.mol |
| Chemical Properties | Back Directory | [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 | [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. | [InChIKey]
DRGAZIDRYFYHIJ-UHFFFAOYSA-N | [CAS DataBase Reference]
1148-79-4(CAS DataBase Reference) | [EPA Substance Registry System]
|
| Hazard Information | Back Directory | [Chemical Properties]
Off-white crystal | [Definition]
ChEBI: A tridentate heterocyclic ligand that binds metals at three meridional sites giving two adjacent 5-membered MN2C2 chelate rings. | [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. | [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. | [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.] |
| Safety Data | Back Directory | [Hazard Codes ]
T+,T | [Risk Statements ]
R27/28:Very Toxic in contact with skin and if swallowed .
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2811 6.1/PG 1
| [WGK Germany ]
3
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
I | [HS Code ]
29333990 |
| Questions And Answer | Back Directory | [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.
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| Spectrum Detail | Back Directory | [Spectrum Detail]
2,2':6',2''-TERPYRIDINE(1148-79-4)MS
2,2':6',2''-TERPYRIDINE(1148-79-4)1HNMR
2,2':6',2''-TERPYRIDINE(1148-79-4)13CNMR
2,2':6',2''-TERPYRIDINE(1148-79-4)IR1
2,2':6',2''-TERPYRIDINE(1148-79-4)IR2
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