9-BBN
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| 9-BBN 0.5 M in THF | |
|---|---|
| Chemical name | 9-Borabicyclo[3.3.1]nonane |
| Chemical formula | C8H15B |
| Molecular mass | 122.02 g/mol |
| Melting point | 153-155 °C (solid dimer) |
| Boiling point | 66 °C (that of THF) |
| Density | 0.894 g/cm³ |
| CAS number | [280-64-8] monomer [21205-91-4] dimer |
| SMILES | |
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| Disclaimer and references | |
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 [1] . 9-BBN is more stable than other boranes in the pure state, this is due to the formation of hydride-bridged dimers in the solid state. The compound is commercially available as a solution in THF, and as a solid. 9-BBN is especially useful in Suzuki reactions.
[edit] External links
- 9-BBN in organic synthesis 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 Tatsuo Ishiyama, Norio Miyaura, and Akira Suzuki Organic Syntheses, Coll. Vol. 9, p.107; Vol. 71, p.89 Article Organic Syntheses publication
- BASF brochure
[edit] References
- ^ Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo[3.3.1]nonane (9-BBN) dimer John A. Soderquist, Herbert C. Brown; J. Org. Chem.; 1981; 46(22); 4599-4600. Abstract
