Diphenylzinc

Diphenylzinc

Names
IUPAC name Diphenylzinc
Identifiers
CAS Number	1078-58-6 Y
3D model (JSmol)	Interactive image
Beilstein Reference	3603125
ChEBI	CHEBI:51499
ChemSpider	10395624 Y
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/c2*1-2-4-6-5-3-1;/h2*1-5H; N Key: MKRVHLWAVKJBFN-UHFFFAOYSA-N N
SMILES C1([Zn]C2=CC=CC=C2)=CC=CC=C1
Properties
Chemical formula	Zn(C6H5)2
Molar mass	219.59 g·mol−1
Appearance	White crystals[1]
Melting point	107 °C (225 °F; 380 K)[1]
Boiling point	280–285 °C (536–545 °F; 553–558 K)[1]
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H228, H250
Precautionary statements	P210, P222, P240, P241, P280, P302+P334, P370+P378, P422
Related compounds
Related compounds	Diphenylcadmium Diphenylmercury Dimethylzinc Diethylzinc Phenylcopper Phenyllithium Phenylsodium
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

Diphenylzinc is an organozinc compound with the chemical formula Zn(C₆H₅)₂, often abbreviated as ZnPh₂, where Ph is phenyl. It is in a form of white crystals. 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, where Ph is phenyl.^[2]

The dimeric solid state form of diphenylzinc.

Diphenylzinc is commercially available. It may be prepared by reaction of phenyllithium with zinc bromide:^[3]

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.^[4][5]