Cyclopentadienyl magnesium bromide

Cyclopentadienyl magnesium bromide
Skeletal formula
Identifiers
CAS Number
  • 17306-10-4
3D model (JSmol)
  • Interactive image
PubChem CID
  • 87410419
InChI
  • InChI=1S/C5H5.BrH.Mg/c1-2-4-5-3-1;;/h1-3H,4H2;1H;/q-1;;+2/p-1
    Key: MFWGSTMYJJJWEV-UHFFFAOYSA-M
  • C1C=CC=[C-]1.[Mg+2].[Br-]
Properties
Chemical formula
 C5H5BrMg
Molar mass 169.304 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Cyclopentadienyl magnesium bromide is a chemical compound with the molecular formula C5H5MgBr. The molecule consists of a magnesium atom bonded to a bromine atom and a cyclopentadienyl group, a ring of five carbons each with one hydrogen atom.

The compound is a Grignard reagent, a type of organometallic compound that features a magnesium atom bonded to a halogen atom and to a carbon atom of some organic functional group.

This compound is of historic importance as the starting material for the first published synthesis of ferrocene by Peter Pauson and Thomas J. Kealy in 1951.[1]

Preparation

The compound can be prepared by reacting cyclopentadiene with magnesium and bromoethane in anhydrous benzene.[2]

References

  1. ^ H. Werner (2012): "At Least 60 Years of Ferrocene: The Discovery and Rediscovery of the Sandwich Complexes". Angewandte Chemie International Edition, volume 51, issue 25, pages 6052–6058. doi:10.1002/anie.201201598
  2. ^ P. L. Pauson and T. J. Kealy (1951): "A New Type of Organo-Iron Compound". Nature, volume 168, issue 4285, pages 1039–1040. doi:10.1038/1681039b0
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Salts and covalent derivatives of the Cyclopentadienide ion
CpH He
LiCp Be B CpMe N C5H4O F Ne
NaCp MgCp2

MgCpBr

Al Si P S Cl Ar
K CaCp2 ScCp3 TiCp2Cl2

(TiCp2Cl)2
TiCpCl3
TiCp2S5
TiCp2(CO)2
TiCp2Me2

VCp2

VCpCh
VCp2Cl2
VCp(CO)4

CrCp2

(CrCp(CO)3)2

MnCp2 FeCp2

Fe(η5-C5H4Li)2
((C5H5)Fe(C5H4))2
(C5H4-C5H4)2Fe2
FeCp2PF6
FeCp(CO)2I

CoCp2

CoCp(CO)2

NiCp2

NiCpNO

Cu Zn Ga Ge As Se Br Kr
Rb Sr Y(C5H5)3 ZrCp2Cl2

ZrCp2ClH

NbCp2Cl2 MoCp2H2

MoCp2Cl2
(MoCp(CO)3)2

Tc RuCp2

RuCp(PPh3)2Cl
RuCp(MeCN)3PF6

RhCp2 PdCp(C3H5) Ag Cd InCp SnCp2 Sb Te I Xe
Cs Ba * LuCp3 HfCp2Cl2 Ta (WCp(CO)3)2 ReCp2H OsCp2 IrCp2 Pt Au Hg TlCp PbCp2 Bi Po At Rn
Fr Ra ** Lr Rf Db Sg Bh HsCp2 Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
 
* LaCp3 CeCp3 PrCp3 NdCp3 PmCp3 SmCp3 Eu Gd Tb DyCp3 Ho ErCp3 TmCp3 YbCp3
** Ac ThCp3
ThCp4 		Pa UCp4 Np Pu Am Cm Bk Cf Es Fm Md No


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