Article · Wikipedia archive · Last revised Jul 30, 2026

Stannocene

Stannocene is an organometallic compound with the formula Sn(C5H5)2. It appears yellow-brown, and melts around 105 °C.

Last revised
Jul 30, 2026
Read time
≈ 1 min
Length
308 w
Citations
7
Source
Wikipedia ↗
Stannocene
source ↗
Names
IUPAC name
  • Stannocene
  • Bis(η5-cyclopentadienyl)tin(II)
Other names
  • Bis(cyclopentadienyl)tin
  • Di(cyclopentadienyl)tin
Identifiers
3D model (JSmol)
  • InChI=1S/2C5H5.Sn/c2*1-2-4-5-3-1;/h2*1-5H;/q2*-1;+2
    Key: CRQFNSCGLAXRLM-UHFFFAOYSA-N
  • [cH-]1cccc1.[cH-]1cccc1.[Sn+2]
Properties
C10H10Sn
Molar mass 248.900 g·mol−1
Melting point 105 °C (221 °F; 378 K)2
Structure3
orthorhombic
Pbcm, No. 57
a = 5.835 Å, b = 25.385 Å, c = 12.785 Å
8 formula per cell
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Stannocene is an organometallic compound with the formula Sn(C5H5)2. It appears yellow-brown, and melts around 105 °C.4

Chemically, stannocene is a metallocene that can be produced efficiently from cyclopentadienyl sodium and tin(II) chloride.5 Unlike in ferrocene the two cyclopentadienyl rings are not parallel.6

Stannocene reacts with strong Lewis acids to give the cyclopentadienyltin(II) cation, SnC5H+
5.7

References

References

  1. Stannocene
  2. Greenwood, Norman N.; Earnshaw, Alan (1984). Chemistry of the Elements. Oxford: Pergamon Press. p. 462. ISBN 978-0-08-022057-4.
  3. Atwood, Jerry L.; Hunter, William E; Cowley, Alan H.; Jones, Richard A.; Stewart, Constantine A. "X-Ray Crystal Structures of Bis(cyclopentadienyl)tin and Bis(pentamethylcyclopentadienyl)lead". J. Chem. Soc., Chem. Commun.
  4. Fischer, E. O.; Grubert, H. (1956) [15 May 1956]. "Di-cyclopentadienyl-zinn" [Bis(cyclopentadienyl)tin]. Zeitung Für Naturforschung B (in German). 11 (7): 423–424. doi:10.1515/znb-1956-0714. (Links go to multiple-article compendium.)
  5. Janiak, Christpher (2010), "Stannocene as cyclopentadienyl transfer agent in transmetallation reactions with lanthanide metals for the synthesis of tris(cyclopentadienyl)lanthanides", Zeitschrift für anorganische und allgemeine Chemie, 636 (13–14): 2387–2390, Bibcode:2010ZAACh.636.2387J, doi:10.1002/zaac.201000239
  6. Smith, P. J. (2012). Chemistry of Tin. Springer Science & Business Media. ISBN 9789401149389.
  7. Schleep, Mario; Hettich, Clarissa; Velázquez Rojas, Jennifer; Kratzert, Daniel; Ludwig, Thilo; Lieberth, Katharina; Krossing, Ingo (2017-03-06). "The Parent Cyclopentadienyltin Cation, Its Toluene Adduct, and the Quadruple‐Decker [Sn 3 Cp 4 ] 2+". Angewandte Chemie International Edition. 56 (11): 2880–2884. doi:10.1002/anie.201611351. ISSN 1433-7851.