Cyclopentadienylthallium

Cyclopentadienylthallium
Names
	IUPAC name Thallium(I) cyclopentadienide
	Other names Thallium cyclopentadienide; (η5-Cyclopentadienyl)thallium
Identifiers
CAS Number	34822-90-7;
3D model (JSmol)	Interactive image;
ChemSpider	24721800 ;
ECHA InfoCard	100.047.466
PubChem CID	97304;
	InChI InChI=1S/C5H5.Tl/c1-2-4-5-3-1;/h1-5H;/q-1;+1 Key: CVEQRUADOXXBRI-UHFFFAOYSA-N; InChI=1/C5H5.Tl/c1-2-4-5-3-1;/h1-5H;/q-1;+1 Key: CVEQRUADOXXBRI-UHFFFAOYAE;
	SMILES [cH-]1cccc1.[Tl+];
Properties
Chemical formula	C5H5Tl
Molar mass	269.48 g·mol−1
Appearance	Light yellow solid
Melting point	300 °C (572 °F; 573 K)
Solubility in water	Insoluble
Hazards
NFPA 704 (fire diamond)	3 0 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cyclopentadienylthallium, also known as thallium cyclopentadienide, is an organothallium compound with formula C₅H₅Tl. This light yellow solid is insoluble in most organic solvents, but sublimes readily. It is used as a precursor to transition metal and main group cyclopentadienyl complexes, as well as organic cyclopentadiene derivatives.^[1]

Preparation and structure

Cyclopentadienylthallium is prepared by the reaction of thallium(I) sulfate, sodium hydroxide, and cyclopentadiene:^[2]

Tl₂SO₄ + 2 NaOH → 2 TlOH + Na₂SO₄

TlOH + C₅H₆ → TlC₅H₅ + H₂O

The compound adopts a polymeric structure, consisting of infinite chains of bent metallocenes. The Tl---Tl---Tl angles are 130°.^[3] Upon sublimation, the polymer cracks into monomers of C_5v symmetry.

Applications

Compared to other cyclopentadienyl (Cp) transfer reagents, such as cyclopentadienyl sodium, CpMgBr and Cp₂Mg, cyclopentadienylthallium is less air sensitive. It is also much less of a reducing agent.

References

^ C. Elschenbroich, (2006). Organometallics. Wiley-VCH, Weinheim. p. 130. ISBN 3-527-29390-6.{{cite book}}: CS1 maint: extra punctuation (link)
^ A.J. Nielson; C.E.F. Rickard; J.M. Smith (1986). "Cyclopentadienylthallium (Thallium Cyclopentadienide)". Inorg. Synth. 24: 97–99. doi:10.1002/9780470132555.ch31.
^ Falk Olbrich, Ulrich Behrens "Crystal structure of catena-cyclopentadienylthallium, [Tl(C₅H₅)]" Zeitschrift für Kristallographie - New Crystal Structures 1997, 212, 47-47.

[1] C. Elschenbroich, (2006). Organometallics. Wiley-VCH, Weinheim. p. 130. ISBN 3-527-29390-6.{{cite book}}: CS1 maint: extra punctuation (link)

[2] A.J. Nielson; C.E.F. Rickard; J.M. Smith (1986). "Cyclopentadienylthallium (Thallium Cyclopentadienide)". Inorg. Synth. 24: 97–99. doi:10.1002/9780470132555.ch31.

[3] Falk Olbrich, Ulrich Behrens "Crystal structure of catena-cyclopentadienylthallium, [Tl(C₅H₅)]" Zeitschrift für Kristallographie - New Crystal Structures 1997, 212, 47-47.

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