Stannocene

{{Chembox

| ImageFile = Stannocene.png

| ImageSize =

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| IUPACName = {{ubl|Stannocene|Bis(η⁵-cyclopentadienyl)tin(II)}}

| OtherNames = {{ubl|Bis(cyclopentadienyl)tin|Di(cyclopentadienyl)tin}}

| Section1 = {{Chembox Identifiers

| CASNo = 1294-75-3

| CASNo_Ref = {{citation|title=Stannocene|url=https://webbook.nist.gov/cgi/formula?ID=C1294753&Mask=20}}

| PubChem =

| SMILES = [cH-]1cccc1.[cH-]1cccc1.[Sn+2]

| StdInChI=1S/2C5H5.Sn/c2*1-2-4-5-3-1;/h2*1-5H;/q2*-1;+2

| StdInChIKey = CRQFNSCGLAXRLM-UHFFFAOYSA-N

}}

| Section2 = {{Chembox Properties

| C=10 | H=10 | Sn=1

| Appearance =

| Density =

| MeltingPtC = 105

| MeltingPt_ref = {{Greenwood&Earnshaw1st|p=462}}

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| Solubility =

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| Section3 = {{Chembox Structure

| Structure_ref={{cite journal|first1=Jerry L.|last1=Atwood|first2=William E|last2=Hunter|first3=Alan H.|last3=Cowley|first4=Richard A.|last4=Jones|first5=Constantine A.| last5=Stewart|title=X-Ray Crystal Structures of Bis(cyclopentadienyl)tin and Bis(pentamethylcyclopentadienyl)lead|journal=J. Chem. Soc., Chem. Commun.}}

| CrystalStruct = orthorhombic

| SpaceGroup = Pbcm, No. 57

| LattConst_a = 5.835 Å

| LattConst_b = 25.385 Å

| LattConst_c = 12.785 Å

| UnitCellFormulas = 8 formula per cell

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| Section4 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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Stannocene is an organometallic compound with the formula {{chem2|Sn(C5H5)2}}. It appears yellow-brown, and melts around 105 °C.{{cite journal|pp=423-424|doi=10.1515/znb-1956-0714|doi-access=free|title=Di-cyclopentadienyl-zinn|trans-title=Bis(cyclopentadienyl)tin|lang=de|first1=E. O.|last1=Fischer|first2=H.|last2=Grubert|journal=Zeitung für Naturforschung B|volume=11|year=1956|orig-date=15 May 1956|issue=7}} (Links go to multiple-article compendium.)

Chemically, stannocene is a metallocene that can be produced efficiently from cyclopentadienyl sodium and tin(II) chloride.{{Citation| last = Janiak| first = Christpher| title = Stannocene as cyclopentadienyl transfer agent in transmetallation reactions with lanthanide metals for the synthesis of tris(cyclopentadienyl)lanthanides| journal=Zeitschrift für anorganische und allgemeine Chemie| year = 2010| volume = 636| issue = 13–14| pages = 2387–2390| url = https://hal.archives-ouvertes.fr/hal-00569390/document|doi=10.1002/zaac.201000239}} Unlike in ferrocene the two cyclopentadienyl rings are not parallel.{{cite book|last = Smith|first=P. J.|title=Chemistry of Tin|url=https://books.google.com/books?id=LTTyCAAAQBAJ|year=2012|publisher=Springer Science & Business Media|isbn=9789401149389}}