2-Phenylpyridine

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 ;
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

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).

The compound is prepared by the reaction of phenyl lithium with pyridine:

C₆H₅Li + C₅H₅N → C₆H₅-C₅H₄N + LiH

The reaction of iridium trichloride with 2-phenylpyridine proceeds via cyclometallation to give the chloride-bridged complex:

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.