9-Borabicyclononane

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ImageFile2 = 9-BBN-dimer-xtal-3D-sticks-skeletal.png IUPACName = 9-Borabicyclo [3.3.1] nonane
OtherNames = Borabicyclononane
Section1 = Chembox Identifiers
Abbreviations = 9-BBN
CASNo = 280-64-8
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SMILES = C1(B2)CCCC2CCC1
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Section2 = Chembox Properties
Formula = C₈H₁₅B
MolarMass = 122.02 g/mol
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Density = 0.894 g/cm³
MeltingPt = 153-155 °C
Melting_notes = solid dimer
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Solubility = Reacts
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RPhrases = R11 R14/15 R36/37/38
SPhrases = S7/9 S16 S33 S7/8 S26 S37/39
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9-Borabicyclo [3.3.1] nonane or 9-BBN is an organoborane compound and used in organic chemistry as a hydroboration reagent. It can be prepared from 1,5-cyclooctadiene and a borane-dimethyl sulfide complex, using dimethoxyethane as the reaction solvent. [cite journal | title = Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo [3.3.1] nonane (9-BBN) dimer | author = John A. Soderquist, Herbert C. Brown | journal = J. Org. Chem. | year = 1981 | volume = 46 | issue = 22 | pages = 4599-4600 | doi = 10.1021/jo00335a067]

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9-BBN is more stable than other boranes in the pure state, but not in solution. This is due to the formation of hydride-bridged dimers in the solid state.

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The compound is commercially available as a solution in tetrahydrofuran and as a solid. 9-BBN is especially useful in Suzuki reactions. [OrgSynth | author = Tatsuo Ishiyama, Norio Miyaura, and Akira Suzuki | title = Palladium(0)-catalyzed reaction of 9-alkyl-9-borabicyclo [3.3.1] nonane with 1-bromo-1-phenylthioethene: 4-(3-cyclohexenyl)-2-phenylthio-1-butene | collvol = 9 | collvolpages = 107 | prep = cv9p0107]

References

External links

* [http://www.basf.com/inorganics/pdfs/bulletins/9BBN.pdf BASF brochure]