Misplaced Pages

Diphenylzinc

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Diphenylzinc
Skeletal formula of diphenylzinc monomer
Ball-and-stick model of the diphenylzinc monomer molecule
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 3603125
ChEBI
ChemSpider
ECHA InfoCard 100.012.803 Edit this at Wikidata
EC Number
  • 214-082-2
Gmelin Reference 28161
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/2C6H5.Zn/c2*1-2-4-6-5-3-1;/h2*1-5H;Key: MKRVHLWAVKJBFN-UHFFFAOYSA-N
SMILES
  • C1(C2=CC=CC=C2)=CC=CC=C1
Properties
Chemical formula C12H10Zn
Molar mass 219.59 g·mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable
Signal word Danger
Hazard statements H228, H250
Precautionary statements P210, P222, P240, P241, P280, P302+P334, P370+P378, P422
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Skeletal formula of diphenylzinc dimerBall-and-stick model of the diphenylzinc dimer moleculeThe dimeric solid state form of diphenylzinc.

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

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.

References

  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.
  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
Zinc compounds
Zinc(I)
Organozinc(I) compounds
Zinc(II)
Organozinc(II) compounds
  • Zn(CH3)2
  • Zn(C2H5)2
  • Zn(CH3COO)2
  • Zn(CH(CH3)2)2
  • Zn(C(CH3)3)2
  • Zn(C6H5)2
  • Zn(C3H5O3)2
  • ZnICH2I
    • Categories: