Bis(cyclooctadiene)nickel(0)

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/c2*1-2-4-6-8-7-5-3-1;/h2*1-2,7-8H2; Y

Key: AYHVBQBQROAZHP-UHFFFAOYSA-N Y

* InChI=1/2C8H8.Ni/c2*1-2-4-6-8-7-5-3-1;/h2*1-2,7-8H2;

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

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

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)" (in en). Encyclopedia of Reagents for Organic Synthesis (John Wiley & Sons Ltd): 1–15. doi:10.1002/047084289x.rb118.pub3. ISBN 9780470842898.
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
* xNi(NO2)6
* xNiF4
* xNiCl4
* xNiBr4
* xNiI4

Nickel(III)|

* Ni2O3
* NiOOH

Nickel(IV)|

* K2NiF6
* MNiOx

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*[CID]: Compound ID
*[H228]: Flammable solid
*[H317]: May cause an allergic skin reaction
*[H334]: May cause allergy or asthma symptoms of breathing difficulties if inhaled
*[H350]: May cause cancer
*[H351]: Suspected of causing cancer
*[P201]: Obtain special instructions before use
*[P202]: Do not handle until all safety precautions have been read and understood
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P272]: Contaminated work clothing should not be allowed out of the workplace
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P281]: Use personal protective equipment as required
*[P285]: In case of inadequate ventilation wear respiratory protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+341]: IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P308+313]: IF exposed or concerned: Get medical advice/attention
*[P321]: Specific treatment (see … on this label)
*[P333+313]: If skin irritation or a rash occurs: Get medical advice/attention
*[P342+311]: Call a POISON CENTER or doctor/physician
*[P363]: Wash contaminated clothing before reuse
*[P370+378]: In case of fire: Use … for extinction
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …
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