Lophine

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

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. Its chemiluminescence continues to attract attention.

Lophine and its dihydro analogue amarine (meso-2,4,5-triphenyl-2-imidazoline) were discovered early in the history of organic chemistry (between 1841 and 1847), 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.

References

↑ Radziszewski, B. R. (1877). "Untersuchungen über Hydrobenzamid, Amarin und Lophin". Berichte der Deutschen Chemischen Gesellschaft. 10: 70–75. doi:10.1002/cber.18770100122.
↑ Nakashima, Kenichiro (2003). "Lophine derivatives as versatile analytical tools". Biomedical Chromatography. 17 (2–3): 83–95. doi:10.1002/bmc.226. PMID 12717796.
↑ Huang, Xue-Feng; Song, Yu-Mei; Wang, Xi-Sen; Pang, Jie; Zuo, Jing-Lin; Xiong, Ren-Gen (2006-02-15). "Crystal structures of amarine and isoamarine and copper(I) coordination chemistry with their allylation products". Journal of Organometallic Chemistry. 691 (5): 1065–1074. doi:10.1016/j.jorganchem.2005.10.040. ISSN 0022-328X.
↑ Japp, Francis R.; Robinson, H. H. (1882-01-01). "L.—On the constitution of amarine and lophine". Journal of the Chemical Society, Transactions. 41: 323–329. doi:10.1039/CT8824100323. ISSN 0368-1645.
↑ Bandivadekar, Priyanka V.; Chaturbhuj, Ganesh U. (2024). "Catalyst-free one-pot synthesis of 2,4,5-tri- and 1,2,4,5-tetrasubstituted imidazoles". Journal of Heterocyclic Chemistry. 61 (3): 430–438. doi:10.1002/jhet.4771.

[1] Radziszewski, B. R. (1877). "Untersuchungen über Hydrobenzamid, Amarin und Lophin". Berichte der Deutschen Chemischen Gesellschaft. 10: 70–75. doi:10.1002/cber.18770100122.

[2] Nakashima, Kenichiro (2003). "Lophine derivatives as versatile analytical tools". Biomedical Chromatography. 17 (2–3): 83–95. doi:10.1002/bmc.226. PMID 12717796.

[3] Huang, Xue-Feng; Song, Yu-Mei; Wang, Xi-Sen; Pang, Jie; Zuo, Jing-Lin; Xiong, Ren-Gen (2006-02-15). "Crystal structures of amarine and isoamarine and copper(I) coordination chemistry with their allylation products". Journal of Organometallic Chemistry. 691 (5): 1065–1074. doi:10.1016/j.jorganchem.2005.10.040. ISSN 0022-328X.

[4] Japp, Francis R.; Robinson, H. H. (1882-01-01). "L.—On the constitution of amarine and lophine". Journal of the Chemical Society, Transactions. 41: 323–329. doi:10.1039/CT8824100323. ISSN 0368-1645.

[5] Bandivadekar, Priyanka V.; Chaturbhuj, Ganesh U. (2024). "Catalyst-free one-pot synthesis of 2,4,5-tri- and 1,2,4,5-tetrasubstituted imidazoles". Journal of Heterocyclic Chemistry. 61 (3): 430–438. doi:10.1002/jhet.4771.