| Revision as of 14:22, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 452302112 of page Triphenylborane for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 19:46, 10 December 2024 edit Bernanke's Crossbow (talk | contribs)Extended confirmed users7,844 edits →Synthesis: no need for a redlink if each ion has its own page |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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| verifiedrevid = 428414998 |
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| Watchedfields = changed |
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| Name = Triphenylborane |
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| verifiedrevid = 470616770 |
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| ImageFile = Triphenylborane.png |
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| ImageFile1 = Triphenylborane-from-xtal-1974-3D-balls.png |
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| Name = Triphenylborane |
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| ImageFile = Structural formula of triphenylborane.svg |
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| IUPACName = Triphenylborane |
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| ImageSize = 200px |
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| Section1 = {{Chembox Identifiers |
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| ImageFile1 = Triphenylborane-from-xtal-1974-3D-balls.png |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PIN = Triphenylborane |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 63579 |
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| ChemSpiderID = 63579 |
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| PubChem = 70400 |
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| PubChem = 70400 |
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| InChI = 1/C18H15B/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H |
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| InChI = 1/C18H15B/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H |
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| InChIKey = MXSVLWZRHLXFKH-UHFFFAOYAV |
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| InChIKey = MXSVLWZRHLXFKH-UHFFFAOYAV |
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| SMILES = c3c(B(c1ccccc1)c2ccccc2)cccc3 |
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| SMILES = B(c1ccccc1)(c2ccccc2)c3ccccc3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C18H15B/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H |
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| StdInChI = 1S/C18H15B/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = MXSVLWZRHLXFKH-UHFFFAOYSA-N |
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| StdInChIKey = MXSVLWZRHLXFKH-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 960-71-4 --> |
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| CASNo = 960-71-4 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 6282553L0G |
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| EINECS = 213-504-2 |
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| EINECS = 213-504-2 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>18</sub>H<sub>15</sub>B |
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| Formula = C<sub>18</sub>H<sub>15</sub>B |
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| MolarMass = 242.12 g/mol |
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| MolarMass = 242.12 g/mol |
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| Appearance = White crystals |
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| Appearance = White crystals |
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| Solubility = Insoluble |
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| Solubility = Insoluble |
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| MeltingPt = 142 °C |
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| MeltingPtC = 142 |
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| BoilingPt = 203 °C (15 mmHg) |
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| BoilingPtC = 203 |
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| BoilingPt_notes = (15 mmHg) |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Structure |
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| MolShape = trigonal planar |
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| MolShape = trigonal planar |
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| Dipole = |
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| Dipole = |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| RPhrases = {{R11}} |
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| GHSPictograms = {{GHS02}} |
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| GHSSignalWord = Warning |
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| SPhrases = {{S16}} {{S22}} {{S24/25}} |
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| HPhrases = {{H-phrases|228}} |
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| PPhrases = {{P-phrases|210|240|241|280|370+378}} |
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|Section8={{Chembox Related |
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| OtherFunction = ] cation |
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| OtherFunction_label = ] |
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'''Triphenylborane''', often abbreviated to '''BPh<sub>3</sub>''' where Ph is the ] C<sub>6</sub>H{{su|b=5|p=−}}, is a ] with the ] B(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>. It is a white crystalline solid and is both air and moisture sensitive, slowly forming ] and ]. It is soluble in ] ]s. |
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==Structure and properties== |
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The core of the compound, BC<sub>3</sub>, has a ] structure. The ] groups are rotated at about a 30° angle from the core plane.<ref>{{cite journal |author1=Zettler, F. |author2=Hausen, H. D. |author3=Hess, H. | title = Crystal and Molecular Structure of Triphenylborane | journal = ] | doi = 10.1016/S0022-328X(00)81488-6 | year = 1974 | volume = 72 | pages = 157 | issue = 2}}</ref> |
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Even though triphenylborane and ] are structurally similar, their ]ity is not. BPh<sub>3</sub> is a weak Lewis acid while B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> is a strong Lewis acid due to the ] of the ] atoms. Other boron Lewis acids include BF<sub>3</sub> and BCl<sub>3</sub>.<ref>{{cite journal | author = Erker, G. | title = Tris(pentafluorophenyl)borane: a special boron Lewis acid for special reactions | journal = ] | doi = 10.1039/b503688g | year = 2005 | pages = 1883–90 | pmid = 15909033 | issue = 11}}</ref> |
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==Synthesis== |
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Triphenylborane was first synthesized in 1922.<ref>{{cite journal |author1=E. Krause |author2=R. Nitsche |name-list-style=amp | title = Darstellung von organischen Bor-Verbindungen mit Hilfe von Borfluorid, II.: Bortriphenyl und Phenyl-borsäure | journal = ] | doi = 10.1002/cber.19220550513 | year = 1922 | volume = 55 | pages = 1261 | issue = 5|url=https://zenodo.org/record/1426723 }}</ref> It is typically made with ] and the ], ].<ref>{{cite book |author1=R. Köster |author2=P. Binger |author3=W. Fenzl |title=Inorganic Syntheses |chapter=Triphenylborane |name-list-style=amp | journal = ] | doi = 10.1002/9780470132463.ch30 | year = 1974 | volume = 15 | pages = 134–136 | isbn = 978-0-470-13246-3}}</ref> |
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: BF<sub>3</sub>•O(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub> + 3 C<sub>6</sub>H<sub>5</sub>MgBr → B(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub> + 3 MgBrF + (C<sub>2</sub>H<sub>5</sub>)<sub>2</sub>O |
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Triphenylborane can also be synthesized on a smaller scale by the ] of ] ].<ref>{{cite journal |author1=G. Wittig |author2=P. Raff | title = Über Komplexbildung mit Triphenyl-bor | journal = ] | doi = 10.1002/jlac.19515730118 | year = 1951 | volume = 573 | pages = 195}}</ref> |
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: → B(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub> + N(CH<sub>3</sub>)<sub>3</sub> + C<sub>6</sub>H<sub>6</sub> |
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==Applications== |
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Triphenylborane is made commercially by a process developed by ] for use in its ] of ] to ], a ] intermediate. ] produces triphenylborane by reacting ] metal, a ] (]), and a secondary ].<ref name = "Guibert">C. R. Guibert and J. L. Little, “Alkyl- and Arylboranes,” ''Ullmanns’s Encyclopedia of Industrial Chemistry'', Wiley-VCH Verlag, Weinheim, 2005. {{doi|10.1002/14356007.a04_309}}</ref> |
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Triphenylborane can be used to make ]es, such as ]. Triarylborane amine complexes are used as ]s for the ] of ]s.<ref name = "Guibert"/> |
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==References== |
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{{reflist}} |
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] |
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] |
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] |