2-Phenylpyridine

2-Phenylpyridine is an organic compound with the formula C₆H₅C₅H₄N (or C₁₁H₉N). It is a colourless viscous liquid. The compound and related derivatives have attracted interest as precursors to highly fluorescent metal complexes of possible value as organic light emitting diodes (OLEDs).^[1]

Quick facts Names, Identifiers ...

2-Phenylpyridine

Names
Preferred IUPAC name 2-Phenylpyridine
Other names 2-Azabiphenyl
Identifiers
CAS Number	1008-89-5
3D model (JSmol)	Interactive image
ChemSpider	13286
ECHA InfoCard	100.012.512
EC Number	213-763-1
MeSH	C058324
PubChem CID	13887
UNII	2Y6S09838Q Y
CompTox Dashboard (EPA)	DTXSID6074417
InChI InChI=1S/C11H9N/c1-2-6-10(7-3-1)11-8-4-5-9-12-11/h1-9H Key: VQGHOUODWALEFC-UHFFFAOYSA-N InChI=1/C11H9N/c1-2-6-10(7-3-1)11-8-4-5-9-12-11/h1-9H Key: VQGHOUODWALEFC-UHFFFAOYAS
SMILES c1ccc(cc1)c2ccccn2
Properties
Chemical formula	C11H9N
Molar mass	155.200 g·mol−1
Appearance	Colorless oil
Density	1.086 g/mL
Boiling point	268–270 °C (514–518 °F; 541–543 K)
Solubility in water	Low
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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The compound is prepared by the reaction of phenyl lithium with pyridine:^[2]

C₆H₅Li + C₅H₅N → C₆H₅-C₅H₄N + LiH

The reaction of iridium trichloride with 2-phenylpyridine proceeds via cyclometallation to give the chloride-bridged complex:^[3][4]

4 C₆H₅-C₅H₄N + 2 IrCl₃(H₂O)₃ → Ir₂Cl₂(C₆H₄-C₅H₄N)₄ + 4 HCl

This complex can be converted to the pictured tris(cyclometallated) derivative tris(2-phenylpyridine)iridium.

The degree and regiochemistry of fluorination of metalated 2-phenylpyridine ligands in platinum(II) complexes significantly modifies the emission properties of the complexes.^[5]