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Skeletal formula of borole
Ball-and-stick model of the borole molecule
Space-filling model of the borole molecule
IUPAC name
287-87-6 YesY
ChemSpider 10709008 N
Jmol-3D images Image
Molar mass 63.89 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

Borole is a theoretical heterocyclic organic compound, a five-membered ring with the formula C4H4BH. It is classified as a metallole. It can be viewed as an structural analog of pyrrole, with boron replacing the nitrogen atom of pyrrole. The unsubstituted compound has not been isolated. Substituted derivatives, which have been synthesized, are called boroles. Although the Hückel's rule cannot be strictly applied to borole, it is considered to be anti-aromatic.[1]


The first borole to be isolated, pentaphenylborole, can be formed by the reaction of 1,1-dimethyl-2,3,4,5-tetraphenylstannole and phenylboron dichloride.[2] Boroles can be used to form ferrocene-like sandwich compounds.[3]


See also[edit]


  1. ^ Alan R. Katritzky, ed. (1993), Advances in Heterocyclic Chemistry 56, Academic Press, p. 375, ISBN 978-0-12-020756-5, retrieved 2010-03-13 
  2. ^ Francis Gordon Albert Stone, Robert West, ed. (1996), Advances in Heterocyclic Chemistry 39, Academic Press, p. 380, ISBN 978-0-12-031139-2, retrieved 2010-03-13 
  3. ^ Alan R. Katritzky, ed. (2001), Advances in Heterocyclic Chemistry 79, Academic Press, pp. 169–170, ISBN 978-0-12-020779-4, retrieved 2010-03-13