Bis(cyclooctadiene)nickel(0)

Bis(cyclooctadiene)nickel(0)

Names
Other names nickel biscod
Identifiers
CAS Number	1295-35-8
3D model (Jmol)	Interactive image
ChemSpider	17215769
ECHA InfoCard	100.013.702
PubChem	6433264
RTECS number	QR6135000
InChI InChI=1S/2C8H8.Ni/c2*1-2-4-6-8-7-5-3-1;/h2*1-2,7-8H2; Key: AYHVBQBQROAZHP-UHFFFAOYSA-N InChI=1/2C8H8.Ni/c2*1-2-4-6-8-7-5-3-1;/h2*1-2,7-8H2; Key: AYHVBQBQROAZHP-UHFFFAOYAH
SMILES C1C[C][C]CC[C][C]1.C1C[C][C]CC[C][C]1.[Ni]
Properties
Chemical formula	C16H24Ni
Molar mass	275.06 g/mol
Appearance	Yellow solid
Melting point	60 °C (140 °F; 333 K) (decomposes)
Hazards
R-phrases	R10 R40
S-phrases	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) is the organometallic compound with the formula Ni(C₈H₁₂)₂. This air-sensitive yellow solid is a common source of Ni(0) in chemical synthesis.^[1]

Ni(cod)₂, as it is commonly abbreviated, 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 benzene and THF.^[2] The cod ligands are easily displaced by phosphines, phosphites, and isocyanides.

References

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: 94–98. doi:10.1002/9780470132593.ch25. ISBN 978-0-470-13259-3.