Year 9 BCwas either a common year starting on Wednesday, Thursdayor Fridayor a leap year starting on Thursday(link will display the full calendar) of the Julian calendar(the sources differ, see leap year errorfor further information) and a leap year starting on Mondayof the Proleptic Julian calendar. 8,651 Followers, 512 Following, 33 Posts - See Instagram photos and videos from @9hb. Learn 9b lessons english 10 with free interactive flashcards. Choose from 500 different sets of 9b lessons english 10 flashcards on Quizlet.
Names | |
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IUPAC name | |
Other names Borabicyclononane Banana borane | |
Identifiers | |
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Abbreviations | 9-BBN |
ChemSpider | |
ECHA InfoCard | |
EC Number |
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UNII | |
CompTox Dashboard(EPA) | |
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Properties | |
C16H30B2 | |
Molar mass | 244.04 g·mol−1 |
Density | 0.894 g/cm3 |
Melting point | 153 to 155 °C (307 to 311 °F; 426 to 428 K) |
Reacts | |
Hazards | |
GHS pictograms | |
GHS Signal word | Warning |
H250, H260, H314 | |
P210, P222, P223, P231+232, P260, P264, P280, P301+330+331, P302+334, P303+361+353, P304+340, P305+351+338, P310, P321, P335+334, P363, P370+378, P402+404, P405, P422, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
verify (what is ?) | |
Infobox references |
9-Borabicyclo[3.3.1]nonane or 9-BBN is an organoborane compound. This colourless solid is used in organic chemistry as a hydroborationreagent. The compound exists as a hydride-bridged dimer, which easily cleaves in the presence of reducible substrates.[1] 9-BBN is also known by its nickname 'banana borane'.[2] This is because rather than drawing out the full structure, chemists often simply draw a banana shape with the bridging boron.[3][better source needed]
Preparation[edit]
Greatest r and b hits download. 9-BBN is prepared by the reaction of 1,5-cyclooctadiene and borane usually in ethereal solvents, for example:[4][5] 1984 news articlesmr. beckers classroom.
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The compound is commercially available as a solution in tetrahydrofuran and as a solid. 9-BBN is especially useful in Suzuki reactions.[6][7][8]
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.
References[edit]
- ^Brown, H. C. (1975). Organic Syntheses via Boranes. New York: John Wiley & Sons. ISBN0-471-11280-1.
- ^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.
- ^'Molecules with Silly or Unusual Names - page 3'. Chm.bris.ac.uk. 2014-05-07. Retrieved 2016-06-01.
- ^Soderquist, John A.; Brown, Herbert C. (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.
- ^Soderquist, John A.; Alvin, Negron (1998). '9-Borabicyclo[3.3.1]nonane Dimer'. Organic Syntheses.; Collective Volume, 9, p. 95
- ^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.; Collective Volume, 9, p. 107
- ^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: 2801. doi:10.1002/anie.199628011.
- ^Liu, J.; Lotesta, S. D.; Sorensen, E. J. (2011). 'A concise synthesis of the molecular framework of pleuromutilin'. Chem. Commun. 47: 1500. doi:10.1039/C0CC04077K. PMC3156455. PMID21079876.