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Structural formula of stibole with an explicit hydrogen
Ball-and-stick model of the stibole molecule
IUPAC name
288-04-0 N
Jmol 3D model Interactive image
Molar mass 174.84 g·mol−1
Related compounds
Related compounds
Pyrrole, phosphole, arsole, bismole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Stibole is a theoretical heterocyclic organic compound, a five-membered ring with the formula C4H4SbH. It is classified as a metallole. It can be viewed as a structural analog of pyrrole, with antimony replacing the nitrogen atom of pyrrole. Substituted derivatives, which have been synthesized, are called stiboles.


2,5-Dimethyl-1-phenyl-1H-stibole, for example, can be formed by the reaction of 1,1-dibutyl-2,5-dimethylstannole and dichlorophenylstibine.[1] Stiboles can be used to form ferrocene-like sandwich compounds.[2]

See also[edit]


  1. ^ J.I.G. Cadogan; S.V. Ley; G. Pattenden; R.A. Raphael; C.W. Rees, eds. (1996), Dictionary of Organic Compounds, 3 (6 ed.), Chapman & Hall, p. 2710, ISBN 978-0-412-54090-5, retrieved 2010-03-04 
  2. ^ A.R. Katritzky; Otto Meth-Cohn; C.W. Rees, eds. (1995), Comprehensive Organic Functional Group Transformations, 4, Elsevier, pp. 1038–1040, ISBN 978-0-08-042325-8, retrieved 2010-03-04