2,2'-Biquinoline

2,2′-Biquinoline is an organic compound with the formula (C9H6N)2. It is one of several biquinolines. It is prepared by reductive coupling of 2-chloroquinoline.[2] It is a colorimetric indicator for organolithium compounds.[3]

2,2′-Biquinoline
Names
Preferred IUPAC name
2,2′-Biquinoline
Other names
2,2′-Biquinolyl; 2-Quinolin-2-ylquinoline; Cuproin
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.961
EC Number
  • 204-357-5
UNII
  • InChI=1S/C18H12N2/c1-3-7-15-13(5-1)9-11-17(19-15)18-12-10-14-6-2-4-8-16(14)20-18/h1-12H
    Key: WPTCSQBWLUUYDV-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C=CC(=N2)C3=NC4=CC=CC=C4C=C3
Properties
C18H12N2
Molar mass 256.308 g·mol−1
Appearance White solid
Density 1.374 g/cm3[1]
Melting point 194.5 °C (382.1 °F; 467.6 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ligand properties
Structure of PdBr2(2,2'-biquinoline).[4]

2,2′-Biquinoline is a bidentate ligand. Unlike the related complexes of 2,2′-bipyridine, the metal does not typically occupy the plane of the biquinoline.

References
  1. Folting, K.; Merritt, L. L. (1977). "2,2'-Biquinolyl". Acta Crystallographica Section B. 33 (11): 3540–3542. doi:10.1107/S0567740877011406.
  2. Nelson, Todd D.; Crouch, R. David (2004). "Cu, Ni, and Pd Mediated Homocoupling Reactions in Biaryl Syntheses: The Ullmann Reaction". Organic Reactions. 15: 265–555. doi:10.1002/0471264180.or063.03. ISBN 0471264180.
  3. Watson, Spencer Charles; Eastham, Jerome F. (1967). "Colored Indicators for Simple Direct Titration of Magnesium and Lithium Reagents". Journal of Organometallic Chemistry. 9: 165–8. doi:10.1016/S0022-328X(00)92418-5.
  4. Ha, Kwang (2012). "(2,2′-Biquinoline-κ2-N,N′)dibromidopalladium(II)". Acta Crystallographica Section E. 68 (5): m618. doi:10.1107/S1600536812015425. PMC 3344352. PMID 22590118.
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