Bis(Cyclooctadiene)Nickel(0)

Bis(cyclooctadiene)nickel(0)
Names
	Other names nickel biscod, Ni(COD)2
Identifiers
CAS Number	1295-35-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	17215769 ;
EC Number	215-072-0;
PubChem CID	6433264;
RTECS number	QR6135000;
UN number	1325
	InChI InChI=1S/2C8H8.Ni/c21-2-4-6-8-7-5-3-1;/h21-2,7-8H2; Key: AYHVBQBQROAZHP-UHFFFAOYSA-N ; InChI=1/2C8H8.Ni/c21-2-4-6-8-7-5-3-1;/h21-2,7-8H2; Key: AYHVBQBQROAZHP-UHFFFAOYAH;
	SMILES C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni];
Properties
Chemical formula	C16H24Ni
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
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H228, H317, H334, H350, H351
GHS precautionary statements	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).
	verify (what is ?)
	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]

References

↑ Wilke, G. (1988). "Contributions to Organo-Nickel Chemistry". Angewandte Chemie International Edition 27 (1): 185–206. doi:10.1002/anie.198801851.
↑ Schunn, R. A.; Ittel, S. D.; Cushing, M. A. (1990). Bis(1,5-Cyclooctadiene)Nickel(0). 28. 94–98. doi:10.1002/9780470132593.ch25. ISBN 978-0-470-13259-3.
↑ Wender, Paul A.; Smith, Thomas E.; Duong, Hung A.; Louie, Janis; Standley, Eric A.; Tasker, Sarah Z. (2015). "Bis(1,5-cyclooctadiene)nickel(0)" (in en). Encyclopedia of Reagents for Organic Synthesis (John Wiley & Sons Ltd): 1–15. doi:10.1002/047084289x.rb118.pub3.
↑ 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.
↑ 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. PMID 24828188.

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[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). 28. 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)" (in en). 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. PMID 24828188.

v t e Nickel compounds
Nickel(0)	Ni(CO)₄ Ni(COD)₂
Nickel(II)	NiBr₂ NiCO₃ NiCl₂ NiCrO₄ NiF₂ NiI₂ Ni(NO₂)₂ Ni(NO₃)₂ NiO Ni(OH)₂ Ni₃(PO₄)₂ NiS NiSO₄ NiTiO₃ Ni(acac)₂ $x$ Ni(NO₂)₆ $x$ NiF₄ $x$ NiCl₄ $x$ NiBr₄ $x$ NiI₄
Nickel(III)	Ni₂O₃ NiOOH
Nickel(IV)	K₂NiF₆ MNiO_$x$

Names

Other names nickel biscod, Ni(COD)₂
Identifiers
CAS Number	1295-35-8^Y
3D model (JSmol)	Interactive image
ChemSpider	17215769^Y
EC Number	215-072-0
PubChem CID	6433264
RTECS number	QR6135000
UN number	1325
InChI InChI=1S/2C8H8.Ni/c21-2-4-6-8-7-5-3-1;/h21-2,7-8H2;^Y Key: AYHVBQBQROAZHP-UHFFFAOYSA-N^Y InChI=1/2C8H8.Ni/c21-2-4-6-8-7-5-3-1;/h21-2,7-8H2; Key: AYHVBQBQROAZHP-UHFFFAOYAH
SMILES C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni]
Properties
Chemical formula	C₁₆H₂₄Ni
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
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H228, H317, H334, H350, H351
GHS precautionary statements	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).
N verify (what is ^YN ?)
Infobox references