Pinacolborane is the

borane Trihydridoboron, also known as borane or borine, is an unstable and highly reactive molecule with the chemical formula . The preparation of borane carbonyl, BH3(CO), played an important role in exploring the chemistry of boranes, as it indicated ...

with the formula (CH₃)₄C₂O₂BH. Often pinacolborane is abbreviated HBpin. It features a boron hydride functional group incorporated in a five-membered C₂O₂B ring. Like related boron alkoxides, pinacolborane is monomeric. It is a colorless liquid. It features a reactive B-H functional group.

Use in organic synthesis

In the presence of catalysts, pinacolborane hydroborates alkenes and, less rapidly, alkynes. Pinacolborane also affects catalyst-free hydroboration of aldehydes, ketones, and carboxylic acids. Pinacolborane is used in borylation, a form of C-H activation. Dehydrogenation of pinacolborane affords dipinacolatodiborane (B₂pin₂): :2{{nbsp(CH₃)₄C₂O₂BH → (CH₃)₄C₂O₂B-BO₂C₂(CH₃)₄ + H₂

Related compounds

* Catecholborane

References

Organoboron compounds Boranes