Diphenylzinc

Diphenylzinc
Identifiers
CAS Number	1078-58-6 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	3603125
ChEBI	CHEBI:51499;
ChemSpider	10395624 ;
ECHA InfoCard	100.012.803
EC Number	214-082-2;
Gmelin Reference	28161
PubChem CID	517896;
CompTox Dashboard (EPA)	DTXSID50910524 ;
	InChI InChI=1S/2C6H5.Zn/c21-2-4-6-5-3-1;/h21-5H; Key: MKRVHLWAVKJBFN-UHFFFAOYSA-N ;
	SMILES C1([Zn]C2=CC=CC=C2)=CC=CC=C1;
Properties
Chemical formula	C12H10Zn
Molar mass	219.59 g·mol−1
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H228, H250
GHS precautionary statements	P210, P222, P240, P241, P280, P302+334, P370+378, P422
	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

Diphenylzinc is an organozinc compound. It is commonly used as the synthetic equivalent of a Ph⁻ synthon. Solvent-free diphenylzinc exists as dimeric PhZn(μ-Ph)₂ZnPh molecules in the solid state.[1]

The dimeric solid state form of diphenylzinc.

Diphenylzinc is commercially available. It may be prepared by reaction of phenyllithium with zinc bromide:[2]

2 PhLi + ZnBr₂ → Ph₂Zn + 2 LiBr

It may also be prepared by the reaction of phenylmagnesium bromide with zinc chloride or diphenylmercury with zinc metal.[3][4]

References

Markies, Peter R.; Schat, Gerrit; Akkerman, Otto S.; Bickelhaupt, Friedrich; Smeets, Wilberth J. J.; Spek, Anthony L. (1990). "Coordinational behavior of solvent-free diorganylzinc compounds: the remarkable x-ray structure of dimeric diphenylzinc". Organometallics. 9 (8): 2243. doi:10.1021/om00158a022.
Curtin, David Y.; Tveten, John L. (1961). "Reaction of Diarylzinc Reagents with Aryldiazonium Salts. Direct Formation of cis-Azo Compounds". J. Org. Chem. 26 (6): 1764. doi:10.1021/jo01065a017.
Markies, P; Schat, Gerrit; Akkerman, Otto S.; Bickelhaupt, F.; Spek, Anthony L. (1992). "Complexation of diphenylzinc with simple ethers. Crystal structures of the complexes Ph₂Zn·glyme and Ph₂Zn·diglyme". J. Organomet. Chem. 430: 1–13. doi:10.1016/0022-328X(92)80090-K.
Pelletier, Guillaume (2013), "Diphenylzinc", Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/047084289x.rn01548, ISBN 978-0-471-93623-7

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[1] Markies, Peter R.; Schat, Gerrit; Akkerman, Otto S.; Bickelhaupt, Friedrich; Smeets, Wilberth J. J.; Spek, Anthony L. (1990). "Coordinational behavior of solvent-free diorganylzinc compounds: the remarkable x-ray structure of dimeric diphenylzinc". Organometallics. 9 (8): 2243. doi:10.1021/om00158a022.

[2] Curtin, David Y.; Tveten, John L. (1961). "Reaction of Diarylzinc Reagents with Aryldiazonium Salts. Direct Formation of cis-Azo Compounds". J. Org. Chem. 26 (6): 1764. doi:10.1021/jo01065a017.

[markies-3] Markies, P; Schat, Gerrit; Akkerman, Otto S.; Bickelhaupt, F.; Spek, Anthony L. (1992). "Complexation of diphenylzinc with simple ethers. Crystal structures of the complexes Ph₂Zn·glyme and Ph₂Zn·diglyme". J. Organomet. Chem. 430: 1–13. doi:10.1016/0022-328X(92)80090-K.

[4] Pelletier, Guillaume (2013), "Diphenylzinc", Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/047084289x.rn01548, ISBN 978-0-471-93623-7