Lophine

Lophine is the organic compound with the formula (C₆H₅C)₂N₂HCC₆H₅. It is a derivative of imidazole wherein all three carbon atoms have phenyl groups as substituents. A white solid, this compound gave the first example of chemiluminescence when its basic solutions were exposed to air.^[1] Its chemiluminescence continues to attract attention.^[2]

Quick facts Names, Identifiers ...

Lophine

Names
Other names 2,4,5-triphenylimidazole
Identifiers
CAS Number	484-47-9
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL34173
ChemSpider	9815
ECHA InfoCard	100.006.915
EC Number	207-606-6
PubChem CID	10232
UNII	Q6K46G80ZD
CompTox Dashboard (EPA)	DTXSID3022039
InChI InChI=1S/C21H16N2/c1-4-10-16(11-5-1)19-20(17-12-6-2-7-13-17)23-21(22-19)18-14-8-3-9-15-18/h1-15H,(H,22,23) Key: RNIPJYFZGXJSDD-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)C2=C(N=C(N2)C3=CC=CC=C3)C4=CC=CC=C4
Properties
Chemical formula	C21H16N2
Molar mass	296.373 g·mol−1
Appearance	white solid
Density	1,0874 g/cm3
Melting point	275 °C (527 °F; 548 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301
Precautionary statements	P264, P270, P301+P316, P321, P330, P405, P501
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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Lophine and its dihydro analogue amarine (meso-2,4,5-triphenyl-2-imidazoline^[3]) were discovered early in the history of organic chemistry (between 1841 and 1847),^[4] before the development of a structural theory of organic chemistry by Kekulé and Couper in the 1850s. Lophine is prepared by condensation of benzaldehyde, benzil, and ammonia.^[5]