2,9-Dichloro-1,10-phenanthroline

Uses

2,9-Dichloro-1,10-phenanthroline is used in organic building blocks and general reagents.

Synthesis

2,9-Dichlorophenanthroline was synthesized from the compound (CAS:39588-59-5) as starting material in the following steps: compound 3 was reacted with phosphorus pentachloride (2 equiv.) in phosphorus chloride solvent at 110 °C for 18 h to give compound 4 in 88% yield.

structure and hydrogen bonding

2,9-Dichloro-1,10-phenanthroline, C12H6Cl2N2, is almost planar (the r.m.s. deviation of C atoms is 0.04 Å). The C—N and C—C distances indicate the delocalization of the π-electrons in the aromatic fused-ring system.

References

[1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 814 - 824
[2] European Journal of Inorganic Chemistry, 2017, vol. 2017, # 34, p. 4020 - 4027
[3] Chemistry - A European Journal, 2007, vol. 13, # 27, p. 7584 - 7594
[4] Organometallics, 2013, vol. 32, # 21, p. 6511 - 6521
[5] Chemistry - A European Journal, 2014, vol. 20, # 25, p. 7819 - 7829