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Bis Cyclooctadiene Nickel 0
Other names
nickel biscod, Ni(COD)2
  • 1295-35-8 checkY
3D model (JSmol)
ECHA InfoCard 100.013.702 Edit this at Wikidata
EC Number
  • 215-072-0
RTECS number
  • QR6135000
UN number 1325
  • InChI=1S/2C8H8.Ni/c2*1-2-4-6-8-7-5-3-1;/h2*1-2,7-8H2; checkY
  • InChI=1/2C8H8.Ni/c2*1-2-4-6-8-7-5-3-1;/h2*1-2,7-8H2;
  • C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni]
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
GHS pictograms GHS02: FlammableGHS07: HarmfulGHS08: Health hazard
GHS Signal word Danger
H228, H317, H334, H350, H351
P201, P202, P210, P240, P241, P261, P272, P280, P281, P285, P302+352, P304+341, P308+313, P321, P333+313, P342+311, P363, P370+378, P405, P501
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) is the organonickel compound with the formula Ni(C8H12)2, also written Ni(cod)2. It is a diamagnetic coordination complex featuring tetrahedral nickel(0) bound to the alkene groups in two 1,5-cyclooctadiene ligands. This highly air-sensitive yellow solid is a common source of Ni(0) in chemical synthesis.[1]

Preparation and properties

The complex is prepared by reduction of anhydrous nickel(II) acetylacetonate in the presence of the diolefin:

Ni(acac)2 + 2 cod + 2 AlEt3 -> Ni(cod)2 + 2 acacAlEt2 + C2H6 + C2H4

Ni(cod)2 is moderately soluble in several organic solvents.[2][3] One or both 1,5-cyclooctadiene ligands are readily displaced by phosphines, phosphites, bipyridine, and isocyanides. If exposed to air, the solid oxidizes to nickel(II) oxide.[4] As a result, this compound is generally handled in a glovebox.[5]


  1. ^ Wilke, G. (1988). "Contributions to Organo-Nickel Chemistry". Angewandte Chemie International Edition. 27 (1): 185-206. doi:10.1002/anie.198801851.
  2. ^ 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.
  3. ^ 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. John Wiley & Sons Ltd: 1-15. doi:10.1002/047084289x.rb118.pub3.
  4. ^ 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.
  5. ^ 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. PMID 24828188.

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