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Bis(cyclooctadiene)nickel(0) is the organonickel compound with the formula Ni(C8H12)2. This highly air-sensitive yellow solid is a common source of Ni(0) in chemical synthesis.[1] If exposed to air at room temperature, decomposition to nickel(II) oxide is rapid,[2] occurring in minutes. As a result, this compound is generally handled in a glovebox.[3][4]

Other names
nickel biscod, Ni(COD)2
3D model (JSmol)
ECHA InfoCard 100.013.702
RTECS number QR6135000
Molar mass 275.06 g/mol
Appearance Yellow solid
Melting point 60 °C (140 °F; 333 K) (N2, decomposes)
Solubility soluble in benzene, tetrahydrofuran, toluene, diethyl ether, dimethylformamide
R-phrases (outdated) R10 R40
S-phrases (outdated) S36/37
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Bis(cyclooctadiene)nickel(0), or Ni(cod)2, is a diamagnetic coordination complex featuring tetrahedral nickel(0) bound to the alkene groups in two 1,5-cyclooctadiene ligands. The complex is prepared by reduction of anhydrous nickel(II) acetylacetonate in the presence of the diolefin:

1/3 [Ni3(acac)6] + 2 cod + 2 AlEt3 → Ni(cod)2 + 2 acacAlEt2 + C2H6 + C2H4

Ni(cod)2 is moderately soluble in several organic solvents.[5][6] One or both 1,5-cyclooctadiene ligands are readily displaced by phosphines, phosphites, bipyridine, and isocyanides.


  1. ^ Wilke, G. (1988). "Contributions to Organo-Nickel Chemistry". Angewandte Chemie International Edition. 27 (1): 185–206. doi:10.1002/anie.198801851.
  2. ^ Zhu, Kake; D'Souza, Lawrence; Richards, Ryan M. (September 2005). "Planting of bis(1,5-cyclooctadiene) nickel upon silica to harvest NiO (<5 nm) nanoparticles in a silica matrix". Applied Organometallic Chemistry. 19 (9): 1065–1069. doi:10.1002/aoc.974.
  3. ^ "The Garg Research Group at UCLA". Retrieved 18 May 2019.
  4. ^ Tasker, Sarah Z.; Standley, Eric A.; Jamison, Timothy F. (2014). "Recent advances in homogeneous nickel catalysis". Nature. 509 (7500): 299–309. doi:10.1038/nature13274. PMC 4344729.
  5. ^ Schunn, R. A.; Ittel, S. D.; Cushing, M. A. (1990). Bis(1,5-Cyclooctadiene)Nickel(0). Inorganic Syntheses. 28. pp. 94–98. doi:10.1002/9780470132593.ch25. ISBN 978-0-470-13259-3.
  6. ^ Wender, Paul A.; Smith, Thomas E.; Duong, Hung A.; Louie, Janis; Standley, Eric A.; Tasker, Sarah Z. (2015). "Bis(1,5-cyclooctadiene)nickel(0)". Encyclopedia of Reagents for Organic Synthesis. American Cancer Society: 1–15. doi:10.1002/047084289x.rb118.pub3.