9-Borabicyclo[3.3.1]nonane CAS NO.280-64-8

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9-Borabicyclo[3.3.1]nonane (cas 280-64-8) is used in organic chemistry as a hydroboration reagent. The compound exists as a hydride-bridged dimer, which easily cleaves in the presence of reducible substrates. The compound is also commercially available as a solution in tetrahydrofuran. 9-BBN is especially useful in Suzuki reactions. Its highly stereoselective addition on olefins allows the preparation of terminal alcohols by subsequent oxidative cleavage with H2O2 in aq. KOH. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of borane. 9-BBN has excellent regioselectivity in hydroboration of alkenes. It is more sensitive to subtle steric differences than Sia2BH, because the rigid hetereocyclic substituents prevent internal rotation to relieve steric hindrance in the transition state. Reflecting its greater sensitivity to electronic factors, 9-BBN is more reactive towards alkenes than alkynes.