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{{Chembox
{{Chembox
| Verifiedfields = changed
| verifiedrevid = 394158397
| verifiedrevid = 426807310
| ImageFile = diphenylzinc.svg
| ImageFile = diphenylzinc.svg
| ImageSize =200px
| ImageSize = 220px
| ImageAlt =
| ImageAlt = Skeletal formula of diphenylzinc monomer
| ImageFile1 = Diphenylzinc 3D ball.png
| ImageSize1 = 220px
| ImageAlt1 = Ball-and-stick model of the diphenylzinc monomer molecule
| IUPACName =
| IUPACName =
| PIN =
| PIN =
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 1078-58-6
| CASNo = 1078-58-6
| PubChem =
| PubChem = 517896
| SMILES = C1([Zn]C2=CC=CC=C2)=CC=CC=C1}}
| EC_number = 214-082-2
| Section2 = {{Chembox Properties
| ChEBI = 51499
| C = 12 | H = 10 | Zn = 1
| Beilstein = 3603125
| Appearance =
| Density =
| Gmelin = 28161
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| MeltingPt =
| ChemSpiderID = 10395624
| BoilingPt =
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| Solubility = }}
| StdInChI = 1S/2C6H5.Zn/c2*1-2-4-6-5-3-1;/h2*1-5H;
| Section3 = {{Chembox Hazards
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| MainHazards =
| StdInChIKey = MKRVHLWAVKJBFN-UHFFFAOYSA-N
| FlashPt =
| SMILES = C1([Zn]C2=CC=CC=C2)=CC=CC=C1}}
| Autoignition = }}
|Section2={{Chembox Properties
| C=12 | H=10 | Zn=1
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS02}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|228|250}}
| PPhrases = {{P-phrases|210|222|240|241|280|302+334|370+378|422}}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
}}


'''Diphenylzinc''' is an [[organozinc compound]]. It is commonly used as the synthetic equivalent of a a Ph<sup>&minus;</sup> [[synthon]]. Solvent-free diphenylzinc exists as dimeric PhZn(&mu;-Ph)<sub>2</sub>ZnPh molecules in solid state.<ref>{{cite journal | last1 = Markies | first1 = Peter R. | last2 = Schat | first2 = Gerrit | last3 = Akkerman | first3 = Otto S. | last4 = Bickelhaupt | first4 = Friedrich | last5 = Smeets | first5 = Wilberth J. J. | last6 = Spek | first6 = Anthony L. | title = Coordinational behavior of solvent-free diorganylzinc compounds: the remarkable x-ray structure of dimeric diphenylzinc | doi = 10.1021/om00158a022 | year = 1990 | pages = 2243 | volume = 9 | journal = [[Organometallics]]}}</ref>
'''Diphenylzinc''' is an [[organozinc compound]]. It is commonly used as the synthetic equivalent of a Ph<sup>&minus;</sup> [[synthon]]. Solvent-free diphenylzinc exists as dimeric {{Nowrap|PhZn(μ-Ph)<sub>2</sub>ZnPh}} molecules in the solid state.<ref>{{cite journal | last1 = Markies | first1 = Peter R. | last2 = Schat | first2 = Gerrit | last3 = Akkerman | first3 = Otto S. | last4 = Bickelhaupt | first4 = Friedrich | last5 = Smeets | first5 = Wilberth J. J. | last6 = Spek | first6 = Anthony L. | title = Coordinational behavior of solvent-free diorganylzinc compounds: the remarkable x-ray structure of dimeric diphenylzinc | doi = 10.1021/om00158a022 | year = 1990 | pages = 2243 | volume = 9 | journal = [[Organometallics]] | issue = 8}}</ref>


{{Multiple image
:[[File:diphenylzinc dimer.svg|thumb|left|120px|The dimeric solid state form of diphenylzinc]]{{clear-left}}
| align = left
| width = 150
| image1 = Diphenylzinc dimer.svg
| alt1 = Skeletal formula of diphenylzinc dimer
| image2 = Diphenylzinc dimer 3D ball.png
| alt2 = Ball-and-stick model of the diphenylzinc dimer molecule
| footer = The dimeric solid state form of diphenylzinc.
}}
{{clear left}}


Diphenylzinc is commercially available. It may be prepared by reaction of [[phenyllithium]] with [[zinc bromide]]:<ref>{{cite journal | last1 = Curtin | first1 = David Y. | last2 = Tveten | first2 = John L. | journal = [[J. Org. Chem.]] | title = Reaction of Diarylzinc Reagents with Aryldiazonium Salts. Direct Formation of cis-Azo Compounds |
Diphenylzinc is commercially available. It may be prepared by reaction of [[phenyllithium]] with [[zinc bromide]]:<ref>{{cite journal | last1 = Curtin | first1 = David Y. | last2 = Tveten | first2 = John L. | journal = [[J. Org. Chem.]] | title = Reaction of Diarylzinc Reagents with Aryldiazonium Salts. Direct Formation of cis-Azo Compounds |
volume = 26 | pages = 1764 | year = 1961 | doi = 10.1021/jo01065a017}}</ref>
volume = 26 | pages = 1764 | year = 1961 | doi = 10.1021/jo01065a017 | issue = 6}}</ref>


:2 PhLi + ZnBr<sub>2</sub> &rarr; Ph<sub>2</sub>Zn + 2 LiBr
:2 PhLi + ZnBr<sub>2</sub> Ph<sub>2</sub>Zn + 2 LiBr


It may also be prepared by the reaction of [[diphenylmercury]] with zinc metal.<ref name = markies>{{cite journal | last1 = Markies | first1 = P | doi = 10.1016/0022-328X(92)80090-K | title = Complexation of diphenylzinc with simple ethers. Crystal structures of the complexes Ph<sub>2</sub>Zn·glyme and Ph<sub>2</sub>Zn·diglyme | year = 1992 | pages = 1 | volume = 430 | journal = [[J. Organomet. Chem.]]}}</ref>
It may also be prepared by the reaction of [[phenylmagnesium bromide]] with [[zinc chloride]] or [[diphenylmercury]] with zinc metal.<ref name = markies>{{cite journal | last1 = Markies | first1 = P | doi = 10.1016/0022-328X(92)80090-K | title = Complexation of diphenylzinc with simple ethers. Crystal structures of the complexes Ph<sub>2</sub>Zn·glyme and Ph<sub>2</sub>Zn·diglyme | year = 1992 | pages = 1–13 | volume = 430 | journal = [[J. Organomet. Chem.]] | last2 = Schat | first2 = Gerrit | last3 = Akkerman | first3 = Otto S. | last4 = Bickelhaupt | first4 = F. | last5 = Spek | first5 = Anthony L.}}</ref><ref>{{Citation|last=Pelletier|first=Guillaume|title=Diphenylzinc|date=2013|encyclopedia=[[Encyclopedia of Reagents for Organic Synthesis]]|place=Chichester, UK|publisher=John Wiley & Sons, Ltd|language=en|doi=10.1002/047084289x.rn01548|isbn=978-0-471-93623-7}}</ref>


==References==
==References==
{{reflist}}
{{reflist}}
{{Zinc compounds}}


[[Category:Organozinc compounds]]
[[Category:Organozinc compounds]]
[[Category:Phenyl compounds]]

[[zh:二苯基锌]]