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Skeletal formula of bismole
Ball-and-stick model of the bismole molecule
IUPAC name
3D model (JSmol)
Molar mass 262.06 g·mol−1
Related compounds
Related compounds
Pyrrole, phosphole, arsole, stibole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Bismole is a theoretical heterocyclic organic compound, a five-membered ring with the formula C4H4BiH. It is classified as a metallole. It can be viewed as a structural analog of pyrrole, with bismuth replacing the nitrogen atom of pyrrole. The unsubstituted compound has not been isolated due to the high energy of the Bi-H bond. Substituted derivatives, which have been synthesized, are called bismoles.[1]


2,5-Bis(trimethylsilyl)-3,4-dimethyl-1-phenyl-1H-bismole, for example, can be formed by the reaction of (1Z,3Z)-1,4-bis(trimethylsilyl)-1,4-diiodobuta-2,3-dimethyl-1,3-diene and diiodophenylbismuthine. Bismoles can be used to form ferrocene-like sandwich compounds.[2]

See also[edit]


  1. ^ Suzuki, Hitomi; Komatsu, Naoki; Ogawa, Takuji; Murafuji, Toshihiro; Ikegami, Tohru; Matano, Yoshihiro (2001), "4: Bismuth-Containing Heterocycle", Organobismuth Chemistry, Elsevier, pp. 329–344, ISBN 978-0-444-20528-5 
  2. ^ Katritzky, Alan R.; Kirby, Gordon W.; Meth-Cohn, Otto; Rees, Charles W., eds. (1995), Synthesis: Carbon with Two Heteroatoms, Each Attached by a Single Bond, Volume 4 of Comprehensive Organic Functional Group Transformations, Elsevier, pp. 1038–1040, ISBN 978-0-08-042325-8