Borole

Borole

Skeletal formula of borole
Ball-and-stick model of the borole molecule Space-filling model of the borole molecule
Names
IUPAC name 1H-Borole
Identifiers
CAS Number	287-87-6 Y
ChemSpider	10709008 N
Jmol 3D model	Interactive image
InChI InChI=1S/C4H5B/c1-2-4-5-3-1/h1-5H N Key: XQIMLPCOVYNASM-UHFFFAOYSA-N 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
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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.

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. Boroles can be used to form ferrocene-like sandwich compounds.

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See also

• Organoboron chemistry