9-Borabicyclononane
- The correct title of this article is 9-Borabicyclo[3.3.1]nonane. The substitution or omission of any < > [ ] { } is due to technical restrictions.
| 9-Borabicyclo[3.3.1]nonane | |
|---|---|
| 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 InChI | InChI=1S/C8H14B/c1-3-7-5-2-6-8(4-1)9-7/h7-8H,1-6H2 |
| Standard InChIKey | AMKGKYQBASDDJB-UHFFFAOYSA-N |
| CAS number | [] |
| EC number | |
| ChemSpider | |
| SMILES | |
| Properties | |
| Chemical formula | C16H26B2 |
| Molar mass | 244.04 g/mol |
| Appearance | white solid |
| Density | 0.894 g/cm3 |
| Melting point |
153–155 °C |
| Solubility in water | reacts |
| Hazards | |
| EU index number | not listed |
| Related compounds | |
| Other compounds | 9-Borabicyclononane dimer |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| 9-Borabicyclo[3.3.1]nonane dimer | |
|---|---|
 |
 |
| |
| Identifiers | |
| Abbreviations | 9-BBN |
| InChI | InChI=1/C16H30B2/c1-5-13-7-2-8-14(6-1)17(13)19-18(20-17)15-9-3-10-16(18)12-4-11-15/h13-16H,1-12H2 |
| InChIKey | QQDDHBYRUTZKSX-UHFFFAOYAH |
| Standard InChI | InChI=1S/C16H30B2/c1-5-13-7-2-8-14(6-1)17(13)19-18(20-17)15-9-3-10-16(18)12-4-11-15/h13-16H,1-12H2 |
| Standard InChIKey | QQDDHBYRUTZKSX-UHFFFAOYSA-N |
| CAS number | [] |
| ChemSpider | |
| SMILES | |
| Properties | |
| Chemical formula | C16H26B2 |
| Molar mass | 244.04 g/mol |
| Appearance | white solid |
| Density | 0.894 g/cm3 |
| Melting point |
153–155 °C |
| Solubility in water | reacts |
| Hazards | |
| EU index number | not listed |
| 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 hydrogen peroxide in aqueous potassium hydroxide. 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; Wiley: New York, 1975. ISBN 0-471-11280-1.
- ↑ Soderquist, John A.; Brown, Herbert C. Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo[3.3.1nonane (9-BBN) dimer]. J. Org. Chem. 1981, 46 (22), 4599–4600. DOI: 10.1021/jo00335a067.
- ↑ Ishiyama, Tatsuo; Miyaura, Norio; Suzuki, Akira Palladium(0)-catalyzed reaction of 9-alkyl-9-borabicyclo[3.3.1nonane 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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