Borole

Borole

Names
IUPAC name 1H-Borole
Identifiers
CAS Number	287-87-6
ChemSpider	10709008
Jmol interactive 3D	Image
InChI InChI=1S/C4H5B/c1-2-4-5-3-1/h1-5H Key: XQIMLPCOVYNASM-UHFFFAOYSA-N InChI=1/C4H5B/c1-2-4-5-3-1/h1-5H Key: XQIMLPCOVYNASM-UHFFFAOYAW
SMILES C1=CC=CB1
Properties
Chemical formula	C4H5B
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).
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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]

Reactions

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

• Organoboron chemistry

References

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