Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 9-Borabicyclo(3.3.1)nonane: Difference between pages

{{correct title|reason=bracket|title=9-Borabicyclo[3.3.1]nonane}}

|Verifiedfields = changed

|Watchedfields = changed

|Name = 9-Borabicyclo[3.3.1]nonane

|verifiedrevid = 477227844

|ImageFile1 = 9-BBN dimer structure.svg

|ImageSize1 = 80px

|ImageFile2 = 9-BBN-dimer-xtal-3D-sticks-skeletal.png

|ImageFile3 = BBN_Crystals.jpg

|IUPACName = 9-Borabicyclo[3.3.1]nonane

|OtherNames = Borabicyclononane<br>Banana borane

|Section1={{Chembox Identifiers

|Abbreviations = 9-BBN

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C8H15B/c1-3-7-5-2-6-8(4-1)9-7/h7-9H,1-6H2

|CASNo_Ref = {{cascite|changed|??}}

|CASNo = 280-64-8

|EINECS = 206-000-9

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 71299

|PubChem = 6327450

|UNII = 4K4J8L1OG9

|SMILES = B1([H]3)(C2CCCC1CCC2)[H]B34C2CCCC4CCC2

|InChI = 1/C8H15B/c1-3-7-5-2-6-8(4-1)9-7/h7-9H,1-6H2

|InChIKey = FEJUGLKDZJDVFY-UHFFFAOYAE

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = FEJUGLKDZJDVFY-UHFFFAOYSA-N

|Section2={{Chembox Properties

|C=16 | H=30 | B=2

|Density = 0.894 g/cm³

|MeltingPtC = 153 to 155

|Solubility = Reacts

}}

|Section7={{Chembox Hazards

|GHSPictograms = {{GHS02}}{{GHS05}}

|GHSSignalWord = Warning

|HPhrases = {{H-phrases|250|260|314}}

|PPhrases = {{P-phrases|210|222|223|231+232|260|264|280|301+330+331|302+334|303+361+353|304+340|305+351+338|310|321|335+334|363|370+378|402+404|405|422|501}}

}}

}}

'''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.<ref>{{cite book|last=Brown|first=H. C.|title=Organic Syntheses via Boranes|publisher=John Wiley & Sons|location=New York|date=1975|isbn=0-471-11280-1|url-access=registration|url=https://archive.org/details/organicsyntheses0000brow}}</ref> 9-BBN is also known by its nickname 'banana borane'.<ref>{{cite web|last1=Stix|first1=Gary|title=The Straight Dope: A Q&A with the Prof behind the Good Science in Breaking Bad|url=https://blogs.scientificamerican.com/talking-back/the-straight-dope-a-qa-with-the-prof-behind-the-good-science-in-breaking-bad/|website=Scientific American Blog Network|publisher=Nature America, Inc.|access-date=18 June 2017|language=en}}</ref> This is because rather than drawing out the full structure, chemists often simply draw a banana shape with the bridging boron.<ref>{{cite web |last=Yale |first=Acadamy |date=2016-03-14 |title=Yale educational material: Hydroboration |url=http://ursula.chem.yale.edu/~chem220/chem220js/STUDYAIDS/hydroborationMech/HydroborationMech.html |url-status=live |archive-url=https://web.archive.org/web/20240813152524/http://ursula.chem.yale.edu/~chem220/chem220js/STUDYAIDS/hydroborationMech/HydroborationMech.html |archive-date=13 August 2024 |website=Hydroboration Mechanics}}</ref>{{Better source|date=March 2016}}

==Preparation==

9-BBN is prepared by the reaction of [[1,5-cyclooctadiene]] and [[borane]] usually in ethereal solvents, for example:<ref>{{cite journal | title = Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo[3.3.1]nonane (9-BBN) dimer | first1= John A.|last1= Soderquist | first2 = Herbert C.|last2= Brown | author2-link = Herbert C. Brown | journal = [[J. Org. Chem.]] | year = 1981 | volume = 46 | issue = 22 | pages = 4599–4600 | doi = 10.1021/jo00335a067}}</ref><ref>{{OrgSynth | volume = 70 | page = 169 | year= 1982 | title = 9-Borabicyclo[3.3.1]nonane Dimer | first1= John A. |last1=Soderquist | last2 = Alvin |first2=Negron | doi = 10.15227/orgsyn.070.0169}}</ref>

[[File:Synthesis of 9-BBN dimer.png|450px]]

The compound is commercially available as a solution in [[tetrahydrofuran]] and as a solid. 9-BBN is especially useful in [[Suzuki reaction]]s.<ref>{{OrgSynth | first1= Tatsuo|last1= Ishiyama|author2-link=Norio Miyaura|author3-link=Akira Suzuki (chemist) | first2 = Norio |last2=Miyaura | first3 = Akira |last3=Suzuki | title = 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 | collvol = 9 | collvolpages = 107 | prep = cv9p0107}}</ref><ref>{{cite journal|first1=A. |last1=Balog|first2= D. |last2=Meng|first3= T.|last3= Kamenecka|first4= P.|last4= Bertinato|first5= D.-S.|last5= Su|first6= E. J.|last6= Sorensen |first7=S. J. |last7=Danishefsky |title=Total Synthesis of (−)-Epothilone A|journal= [[Angew. Chem. Int. Ed. Engl.]]|date=1996|volume= 35|issue=2324|page= 2801 |doi=10.1002/anie.199628011}}</ref><ref>{{cite journal|first1= J.|last1= Liu|first2= S. D. |last2=Lotesta |first3= E. J. |last3=Sorensen |title=A concise synthesis of the molecular framework of pleuromutilin |journal=Chem. Commun. |date=2011|volume= 47|issue= 5|pages= 1500–1502|doi=10.1039/C0CC04077K |pmid=21079876 |pmc=3156455}}</ref>

Its highly [[regioselective]] addition on [[alkenes]] allows the preparation of terminal [[alcohol (chemistry)|alcohol]]s by subsequent oxidative cleavage with [[hydrogen peroxide|H₂O₂]] in aqueous [[potassium hydroxide|KOH]]. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of borane.

==See also==

* [[Organoboron chemistry]]

* [[Boron]]

==References==

{{Reflist}}

{{DEFAULTSORT:Borabicyclononane, 9-}}

[[Category:Organoboranes]]

[[Category:Reagents for organic chemistry]]