9-Borabicyclononane
- The correct title of this page is 9-Borabicyclo[3.3.1]nonane. It appears incorrectly here because of technical restrictions.
| 9-Borabicyclononane | |
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| 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 InChIKey | AMKGKYQBASDDJB-UHFFFAOYSA-N |
| CAS number | [] |
| EC number | |
| ChemSpider | |
| SMILES | |
| Properties | |
| Chemical formula | C16H26B2 |
| Molar mass | 244.04 g/mol |
| Density | 0.894 g/cm3 |
| Melting point |
153-155 °C |
| Solubility in water | Reacts |
| Hazards | |
| R-phrases | Template:R11 Template:R14/15 Template:R36/37/38 |
| S-phrases | Template:S7/9 Template:S16 Template:S33 Template:S7/8 Template:S26 Template:S37/39 |
| 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.[1] Like other organoboron compounds, 9-BBN is pyrophoric.
9-BBN is prepared by the reaction of 1,5-cyclooctadiene and borane usually in etherial solvents.[2] The compound is commercially available as a solution in tetrahydrofuran and as a solid. 9-BBN is especially useful in Suzuki reactions.[3]
Its highly stereoselective addition on olefins allows the preparation of terminal alcohols by subsequent oxidative cleavage with H2O2 in aq. KOH. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of borane.
References
- ↑ Brown, H. C. “Organic Syntheses via Boranes” John Wiley & Sons, Inc. New York: 1975. ISBN 0-471-11280-1.
- ↑ John A. Soderquist, Herbert C. Brown (1981). "Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo[3.3.1]nonane (9-BBN) dimer". J. Org. Chem. 46 (22): 4599–4600. doi:10.1021/jo00335a067.
- ↑ 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 . Org. Synth., <http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv9p0107>; Coll. Vol., 9, 107
External links
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