Stibole is a heterocyclic organic compound, a five-membered ring with the formula C<sub>4</sub>H<sub>4</sub>SbH. It is classified as a metallole. It can be viewed as a structural analog of pyrrole, with antimony replacing the nitrogen atom of pyrrole. Stibole itself has not been isolated, but many substituted derivatives have been synthesized. They are called stiboles.
Pentaphenylstibile is prepared from 1,4-dilithio-1,2,3,4-tetraphenylbutadiene and phenylantimony dichloride by a salt metathesis reaction:
Even simpler than the above, 1-phenylstibole can be prepared analgously from 1,4-dilithiobutadiene. It is yellow oil that resinifies at room temperature.
2,5-Dimethyl-1-phenyl-1H-stibole, for example, can be formed by the reaction of 1,1-dibutyl-2,5-dimethylstannole and dichlorophenylstibine.
Stibolides () form half-sandwich compounds.