Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Triphenylborane: Difference between pages

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470616770

| Name = Triphenylborane

| ImageFile = Structural formula of triphenylborane.svg

| ImageSize = 200px

| ImageFile1 = Triphenylborane-from-xtal-1974-3D-balls.png

| PIN = Triphenylborane

|Section1={{Chembox Identifiers

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

| SMILES = B(c1ccccc1)(c2ccccc2)c3ccccc3

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 960-71-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6282553L0G

|Section2={{Chembox Properties

| Formula = C₁₈H₁₅B

| MolarMass = 242.12 g/mol

| Appearance = White crystals

| Solubility = Insoluble

| MeltingPtC = 142

| BoilingPtC = 203

| BoilingPt_notes = (15 mmHg)

|Section3={{Chembox Structure

| MolShape = trigonal planar

| Dipole =

|Section7={{Chembox Hazards

| GHSPictograms = {{GHS02}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|228}}

| PPhrases = {{P-phrases|210|240|241|280|370+378}}

}}

|Section8={{Chembox Related

| OtherFunction = [[Triphenylmethyl]] cation

| OtherFunction_label = [[isoelectronic]]

'''Triphenylborane''', often abbreviated to '''BPh₃''' where Ph is the [[phenyl group]] C₆H₅-, is a [[chemical compound]] with the [[chemical formula|formula]] B(C₆H₅)₃. It is a white crystalline solid and is both air and moisture sensitive, slowly forming [[benzene]] and [[triphenylboroxine]]. It is soluble in [[aromatic]] [[solvent]]s.

==Structure and properties==

The core of the compound, BC₃, has a [[trigonal planar]] structure. The [[phenyl]] 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 = [[J. Organomet. Chem.]] | doi = 10.1016/S0022-328X(00)81488-6 | year = 1974 | volume = 72 | pages = 157 | issue = 2}}</ref>

Even though triphenylborane and [[tris(pentafluorophenyl)borane]] are structurally similar, their [[Lewis acid]]ity is not. BPh₃ is a weak Lewis acid while B(C₆F₅)₃ is a strong Lewis acid due to the [[electronegativity]] of the [[fluorine]] atoms. Other boron Lewis acids include BF₃ and BCl₃.<ref>{{cite journal | author = Erker, G. | title = Tris(pentafluorophenyl)borane: a special boron Lewis acid for special reactions | journal = [[Dalton Trans.]] | doi = 10.1039/b503688g | year = 2005 | pages = 1883–90 | pmid = 15909033 | issue = 11}}</ref>

==Synthesis==

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 = [[Chemische Berichte]] | 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 [[boron trifluoride diethyl etherate]] and the [[Grignard reagent]], [[phenylmagnesium bromide]].<ref>{{cite book |author1=R. Köster |author2=P. Binger |author3=W. Fenzl |title=Inorganic Syntheses |chapter=Triphenylborane |name-list-style=amp | journal = [[Inorg. Synth.]] | doi = 10.1002/9780470132463.ch30 | year = 1974 | volume = 15 | pages = 134–136 | isbn = 978-0-470-13246-3}}</ref>

: BF₃•O(C₂H₅)₂ + 3 C₆H₅MgBr → B(C₆H₅)₃ + 3 MgBrF + (C₂H₅)₂O

Triphenylborane can also be synthesized on a smaller scale by the [[thermal decomposition]] of [[trimethylammonium tetraphenylborate]].<ref>{{cite journal |author1=G. Wittig |author2=P. Raff | title = Über Komplexbildung mit Triphenyl-bor | journal = [[Liebigs Annalen der Chemie]] | doi = 10.1002/jlac.19515730118 | year = 1951 | volume = 573 | pages = 195}}</ref>

: [B(C₆H₅)₄][NH(CH₃)₃] → B(C₆H₅)₃ + N(CH₃)₃ + C₆H₆

==Applications==

Triphenylborane is made commercially by a process developed by [[DuPont (1802–2017)|Du Pont]] for use in its [[hydrocyanation]] of [[butadiene]] to [[adiponitrile]], a [[nylon]] intermediate. [[DuPont (1802–2017)|Du Pont]] produces triphenylborane by reacting [[sodium]] metal, a [[haloaromatic]] ([[chlorobenzene]]), and a secondary [[alkyl borate ester]].<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>

Triphenylborane can be used to make [[triarylborane amine complex]]es, such as [[pyridine-triphenylborane]]. Triarylborane amine complexes are used as [[catalyst]]s for the [[polymerization]] of [[acrylic ester]]s.<ref name = "Guibert"/>

==References==

{{reflist}}

[[Category:Organoboranes]]

[[Category:Phenyl compounds]]

[[Category:Substances discovered in the 1920s]]