Difference between revisions of "9-Borabicyclononane"
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| Abbreviations = 9-BBN | | Abbreviations = 9-BBN | ||
| CASNo = 280-64-8 | | CASNo = 280-64-8 | ||
| − | | EINECS = | + | | EINECS = 206-000-9 |
| + | | ChemSpiderID = 4885947 | ||
| PubChem = | | PubChem = | ||
| SMILES = C1(B2)CCCC2CCC1 | | SMILES = C1(B2)CCCC2CCC1 | ||
| − | | InChI = | + | | InChI = 1/C8H14B/c1-3-7-5-2-6-8(4-1)9-7/h7-8H,1-6H2 |
| + | | InChIKey = AMKGKYQBASDDJB-UHFFFAOYAO | ||
| + | | StdInChIKey = AMKGKYQBASDDJB-UHFFFAOYSA-N | ||
| RTECS = | | RTECS = | ||
| MeSHName = | | MeSHName = | ||
Revision as of 09:41, 16 August 2009
- The correct title of this page is 9-Borabicyclo[3.3.1]nonane. It appears incorrectly here because of technical restrictions.
| 9-Borabicyclononane | |
|---|---|
 |
 |
| |
| 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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This page was originally imported from Wikipedia, specifically this version of the article "9-Borabicyclononane". Please see the history page on Wikipedia for the original authors. This WikiChem article may have been modified since it was imported. It is licensed under the Creative Commons Attribution–Share Alike 3.0 Unported license. |
