9-Borabicyclononane

The correct title of this article is 9-Borabicyclo[3.3.1]nonane. The substitution or omission of any < > [ ] { } is due to technical restrictions.

9-Borabicyclo[3.3.1]nonane IUPAC name 9-Borabicyclo[3.3.1]nonane Other names Borabicyclononane Identifiers Abbreviations 9-BBN InChI InChI=1/C8H14B/c1-3-7-5-2-6-8(4-1)9-7/h7-8H,1-6H2 InChIKey AMKGKYQBASDDJB-UHFFFAOYAO Standard InChI InChI=1S/C8H14B/c1-3-7-5-2-6-8(4-1)9-7/h7-8H,1-6H2 Standard InChIKey AMKGKYQBASDDJB-UHFFFAOYSA-N CAS number [280-64-8] EC number 206-000-9 ChemSpider 4885947 SMILES   C1(B2)CCCC2CCC1 Properties Chemical formula C16H26B2 Molar mass 244.04 g/mol Appearance white solid Density 0.894 g/cm3 Melting point 153–155 °C Solubility in water reacts Hazards EU index number not listed Related compounds Other compounds 9-Borabicyclononane dimer Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

9-Borabicyclo[3.3.1]nonane dimer Identifiers Abbreviations 9-BBN InChI InChI=1/C16H30B2/c1-5-13-7-2-8-14(6-1)17(13)19-18(20-17)15-9-3-10​-16(18)12-4-11-15/h13-16H,1-12H2 InChIKey QQDDHBYRUTZKSX-UHFFFAOYAH Standard InChI InChI=1S/C16H30B2/c1-5-13-7-2-8-14(6-1)17(13)19-18(20-17)15-9-3-1​0-16(18)12-4-11-15/h13-16H,1-12H2 Standard InChIKey QQDDHBYRUTZKSX-UHFFFAOYSA-N CAS number [21205-91-4] ChemSpider 21241191 SMILES   [H]1[B@]5([H][B@@]13C2CCCC3CCC2)C4CCCC5CCC4 Properties Chemical formula C16H26B2 Molar mass 244.04 g/mol Appearance white solid Density 0.894 g/cm3 Melting point 153–155 °C Solubility in water reacts Hazards EU index number not listed Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

9-Borabicyclo[3.3.1]nonane or 9-BBN is an organoborane compound. This colourless solid 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.

9-BBN is prepared by the reaction of 1,5-cyclooctadiene and borane adducts, usually in etherial solvents. The compound is commercially available as a solution in tetrahydrofuran and as a solid.

The solid is a hydride-bridged dimer: solutions in THF and other donor solvents contain monomeric adducts with a solvent molecule, eg 9-BBN·THF.

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 hydrogen peroxide in aqueous potassium hydroxide. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of borane.

External links

• BASF brochure