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9-Borabicyclononane

9-Borabicyclononane

IUPAC name	9-Borabicyclo[3.3.1]nonane
Other names	Borabicyclononane
Identifiers
Abbreviations	9-BBN
CAS number	280-64-8
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

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]

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