9-BBN
From Wikipedia, the free encyclopedia
| 9-BBN | |
|---|---|
 |
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| IUPAC name | 9-Borabicyclo[3.3.1]nonane |
| Other names | Borabicyclononane |
| Identifiers | |
| Abbreviations | 9-BBN |
| CAS number | [] |
| SMILES | C1(B2)CCCC2CCC1 |
| Properties | |
| Molecular formula | C8H15B |
| Molar mass | 122.02 g/mol |
| Density | 0.894 g/cm3 |
| Melting point |
153-155 °C (solid dimer) |
| Solubility in water | Reacts |
| Hazards | |
| R-phrases | R11 R14/15 R36/37/38 |
| S-phrases | S7/9 S16 S33 S7/8 S26 S37/39 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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.[1] 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. The compound is commercially available as a solution in tetrahydrofuran and as a solid. 9-BBN is especially useful in Suzuki reactions.[2]
[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
- ^ Tatsuo Ishiyama, Norio Miyaura, and Akira Suzuki "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." Organic Syntheses, Coll. Vol. 9, p.107; Vol. 71, p.89 Article
