9-Borabicyclo(3.3.1)nonane

Monoclinic (dimer)

C2 / m (dimer)

A = 1454 pm b = 1549 pm c = 688 pm β = 92.7 ° (dimer)

• 9-BBN (monomer)
• (9 -BBN ) 2 ( Dimer )
• Bis- 9- borabicyclo [3.3.1] nonane (dimer)

• C8H15B (monomer)
• C16H30B2 (dimer)

• 280-64-8 (monomer)
• 21205-91-4 (dimer)

Fixed

150-152 ° C

Risk

Template: Infobox chemical / molecular formula search available

9- borabicyclo [3.3.1] nonane, often abbreviated as 9-BBN is an organoborane. The colorless solid is used in the organic chemistry, as a reagent for the hydroboration. The compound is a of the hydrogen atoms linked dimer which is easily cleaved in the presence of a reducible substrate. Like other organoboron compounds is also 9- BBN pyrophoric and is therefore mostly used as a solution in tetrahydrofuran.

As a solid 9- BBN is available exclusively as a dimer, as in certain organic solvents; however, it may be in solution and an equilibrium between dimer and monomer ( with the solvent -complexed ) form.

Representation

9-BBN is prepared by reacting 1,5-cyclooctadiene with borane complexes such as with tetrahydrofuran or dimethyl sulfide, in ethereal solution.

Use

9- BBN can be used in addition to the hydroboration in Suzuki reactions. Due to its high steric hindrance of the substituents leads cyclooctyl - 9- BBN in the hydroboration reaction compared to boranes almost exclusively to the anti-Markovnikov product.