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Diphenylzinc

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Diphenylzinc
Skeletal formula of diphenylzinc monomer
Ball-and-stick model of the diphenylzinc monomer molecule
Names
IUPAC name
Diphenylzinc
Identifiers
3D model (JSmol)
3603125
ChEBI
ChemSpider
ECHA InfoCard100.012.803Edit this at Wikidata
EC Number
  • 214-082-2
28161
  • InChI=1S/2C6H5.Zn/c2*1-2-4-6-5-3-1;/h2*1-5H; ☒N
    Key: MKRVHLWAVKJBFN-UHFFFAOYSA-N ☒N
  • C1([Zn]C2=CC=CC=C2)=CC=CC=C1
Properties
Zn(C6H5)2
Molar mass219.59 g·mol−1
AppearanceWhite crystals[1]
Melting point107 °C (225 °F; 380 K)[1]
Boiling point280–285 °C (536–545 °F; 553–558 K)[1]
Hazards
GHS labelling:
GHS02: Flammable
Danger
H228,H250
P210,P222,P240,P241,P280,P302+P334,P370+P378,P422
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Diphenylzinc is anorganozinc compound with thechemical formulaZn(C6H5)2, often abbreviated asZnPh2, where Ph isphenyl. It is in a form of white crystals. It is commonly used as the synthetic equivalent of aPhsynthon. Solvent-free diphenylzinc exists as dimericPhZn(μ-Ph)2ZnPh molecules in the solid state, where Ph isphenyl.[2]

Skeletal formula of diphenylzinc dimer
Ball-and-stick model of the diphenylzinc dimer molecule
The dimeric solid state form of diphenylzinc.

Diphenylzinc is commercially available. It may be prepared by reaction ofphenyllithium withzinc bromide:[3]

2 PhLi + ZnBr2 → Ph2Zn + 2LiBr

It may also be prepared by the reaction ofphenylmagnesium bromide withzinc chloride ordiphenylmercury with zinc metal.[4][5]

References

[edit]
  1. ^abc"Diphenylzinc | CAS 1078-58-6 | (C6H5)2Zn | AMERICAN ELEMENTS ®".
  2. ^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.
  3. ^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.
  4. ^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.
  5. ^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(I)
Organozinc(I) compounds
Zinc(II)
Organozinc(II) compounds
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