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9-Borabicyclo(3.3.1)nonane

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The correct title of this article is 9-Borabicyclononane. The substitution of any brackets is due to technical restrictions.
9-Borabicyclononane
Names
IUPAC name 9-Borabicyclononane
Other names Borabicyclononane
Banana borane
Identifiers
CAS Number
3D model (JSmol)
Abbreviations 9-BBN
ChemSpider
ECHA InfoCard 100.005.456 Edit this at Wikidata
EC Number
  • 206-000-9
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H15B/c1-3-7-5-2-6-8(4-1)9-7/h7-9H,1-6H2Key: FEJUGLKDZJDVFY-UHFFFAOYSA-N
  • InChI=1/C8H15B/c1-3-7-5-2-6-8(4-1)9-7/h7-9H,1-6H2Key: FEJUGLKDZJDVFY-UHFFFAOYAE
SMILES
  • B1(3)(C2CCCC1CCC2)B34C2CCCC4CCC2
Properties
Chemical formula C16H30B2
Molar mass 244.04 g·mol
Density 0.894 g/cm
Melting point 153 to 155 °C (307 to 311 °F; 426 to 428 K)
Solubility in water Reacts
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: Corrosive
Signal word Warning
Hazard statements H250, H260, H314
Precautionary statements P210, P222, P223, P231+P232, P260, P264, P280, P301+P330+P331, P302+P334, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P335+P334, P363, P370+P378, P402+P404, P405, P422, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

9-Borabicyclononane 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. 9-BBN is also known by its nickname 'banana borane'. This is because rather than drawing out the full structure, chemists often simply draw a banana shape with the bridging boron.

Preparation

9-BBN is prepared by the reaction of 1,5-cyclooctadiene and borane usually in ethereal solvents, for example:

The compound is commercially available as a solution in tetrahydrofuran and as a solid. 9-BBN is especially useful in Suzuki reactions.

Its highly regioselective addition on alkenes allows the preparation of terminal alcohols by subsequent oxidative cleavage with H2O2 in aqueous KOH. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of borane.

See also

References

  1. Brown, H. C. (1975). Organic Syntheses via Boranes. New York: John Wiley & Sons. ISBN 0-471-11280-1.
  2. Stix, Gary. "The Straight Dope: A Q&A with the Prof behind the Good Science in Breaking Bad". Scientific American Blog Network. Nature America, Inc. Retrieved 18 June 2017.
  3. Yale (2016-03-14). "Yale educational material: Hydroboration". Hydroboration Mechanics. Archived from the original on 13 August 2024.
  4. Soderquist, John A.; Brown, Herbert C. (1981). "Simple, remarkably efficient route to high purity, crystalline 9-borabicyclononane (9-BBN) dimer". J. Org. Chem. 46 (22): 4599–4600. doi:10.1021/jo00335a067.
  5. Soderquist, John A.; Alvin, Negron (1982). "9-Borabicyclononane Dimer". Organic Syntheses. 70: 169. doi:10.15227/orgsyn.070.0169.
  6. Ishiyama, Tatsuo; Miyaura, Norio; Suzuki, Akira. "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; Collected Volumes, vol. 9, p. 107.
  7. Balog, A.; Meng, D.; Kamenecka, T.; Bertinato, P.; Su, D.-S.; Sorensen, E. J.; Danishefsky, S. J. (1996). "Total Synthesis of (−)-Epothilone A". Angew. Chem. Int. Ed. Engl. 35 (2324): 2801. doi:10.1002/anie.199628011.
  8. Liu, J.; Lotesta, S. D.; Sorensen, E. J. (2011). "A concise synthesis of the molecular framework of pleuromutilin". Chem. Commun. 47 (5): 1500–1502. doi:10.1039/C0CC04077K. PMC 3156455. PMID 21079876.
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