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<div>{{chembox<br />
| verifiedrevid = 437791930<br />
| ImageFile = Diphenylphosphine.svg<br />
| ImageName = Ball-and-stick model<br />
| ImageFile1 = Diphenylphosphine-3D-balls.png<br />
| ImageName1 = Ball-and-stick model<br />
| ImageFile2 = Diphenylphosphine-3D-vdW.png<br />
| ImageSize2 = 200px<br />
| IUPACName= diphenylphosphane<br />
| Section1 = {{Chembox Identifiers<br />
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}<br />
| ChemSpiderID = 63209<br />
| InChI = 1/C12H11P/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H<br />
| SMILES = c2c(Pc1ccccc1)cccc2<br />
| InChIKey = GPAYUJZHTULNBE-UHFFFAOYAN<br />
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}<br />
| StdInChI = 1S/C12H11P/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H<br />
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}<br />
| StdInChIKey = GPAYUJZHTULNBE-UHFFFAOYSA-N<br />
| CASNo_Ref = {{cascite|correct|CAS}}<br />
| CASNo = 829-85-6<br />
}}<br />
| Section2 = {{Chembox Properties<br />
| Formula = C<sub>12</sub>H<sub>11</sub>P<br />
| MolarMass = 186.19 g/mol<br />
| Appearance = colorless liquid<br />
| Density = 1.07 g/cm<sup>3</sup>, liquid<br />
| Solubility = Insoluble<br />
| BoilingPt = 280 °C (553 K)<br />
}}<br />
| Section3 = {{Chembox Hazards<br />
| RPhrases = 17-36/37/38<br />
| SPhrases = 26-36<br />
| ExternalMSDS = [http://www.alfa.com/MSDSPDF/English_/56169.pdf External MSDS]<br />
}}<br />
}}<br />
'''Diphenylphosphine''', also known as diphenylphosphane, is [[organophosphorus compound]] with the formula (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>PH. This foul-smelling, colorless liquid is easily oxidized in air. It is a precursor to organophosphorus ligands for use as [[catalysts]].<br />
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==Synthesis==<br />
Diphenylphosphine can be prepared cheaply from [[triphenylphosphine]].<ref>{{cite journal | author1 = Wittenberg, D. | author2 = Gilman, H. | authorlink2 = Henry Gilman | title = Lithium Cleavages of Triphenyl Derivatives of Some Group Vb Elements in Tetrahydrofuran | journal = [[Journal of Organic Chemistry]] | year = 1958 | volume = 23 | issue = 7 | pages = 1063–1065 | doi = 10.1021/jo01101a613 }}</ref><br />
:PPh<sub>3</sub> + 2 Li → LiPPh<sub>2</sub> + LiPh<br />
:LiPPh<sub>2</sub> + H<sub>2</sub>O → Ph<sub>2</sub>PH + LiOH<br />
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==Uses and reactions==<br />
In the laboratory, diphenylphosphine is a common intermediate. It can be deprotonated to give diphenylphosphide derivatives:<ref name = piotrowski>{{ cite encyclopedia | author = Piotrowski, D. W. | title = Diphenylphosphine | encyclopedia = Encyclopedia of Reagents for Organic Synthesis | publisher = John Wiley & Sons | location = New York | year = 2001 | doi = 10.1002/047084289X.rd427 }}</ref><br />
:Ph<sub>2</sub>PH + <sup>n</sup>BuLi → Ph<sub>2</sub>PLi + <sup>n</sup>BuH<br />
The preparation of phosphine [[ligand]]s, [[Horner-Wadsworth-Emmons reaction|Wittig-Horner reagents]], and [[phosphonium salt]]s are commonly accomplished by alkylating diphenylphosphine. The hydrogen atom connected to phosphorus undergoes Michael-like addition to activated alkenes, providing products with which to produce phosphine ligands such as [[1,2-bis(diphenylphosphino)ethane]] (Ph<sub>2</sub>PC<sub>2</sub>H<sub>4</sub>PPh<sub>2</sub>). Diphenylphosphine and especially diphenylphosphide derivatives are nucleophiles, so they add to carbon – heteroatom double bonds.<ref name = piotrowski/> For example, in the presence of concentrated hydrochloric acid at 100 °C, diphenylphosphine adds to the carbon atom in [[benzaldehyde]] to give (phenyl-(phenylmethyl)phosphoryl)benzene.<br />
:Ph<sub>2</sub>PH + PhCHO → Ph<sub>2</sub>P(O)CH<sub>2</sub>Ph<br />
<br />
Compared to tertiary phosphines, diphenylphosphine is weakly basic. The pKa of the protonated derivative is 0.03:<ref>C. A. Streuli, "Determination of Basicity of Substituted Phosphines by Nonaqueous Titrimetry", Analytical Chemistry 1960, volume 32, pages 985-987.{{DOI|10.1021/ac60164a027}}</ref><br />
:Ph<sub>2</sub>PH<sub>2</sub><sup>+</sup> <math>\overrightarrow{\leftarrow}</math> Ph<sub>2</sub>PH + H<sup>+</sup><br />
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===Handling properties===<br />
During the handling of diphenylphosphine, care must be taken to avoid oxidation of diphenylphosphine.<ref name = Svara>{{ Ullmann | author = Svara, J.; Weferling, N.; Hofmann, T. | title = Phosphorus Compounds, Organic | doi = 10.1002/14356007.a19_545.pub2 }}</ref> <br />
:Ph<sub>2</sub>PH + O<sub>2</sub> → Ph<sub>2</sub>P(O)OH <br />
The use of the diphenylphosphine–borane complex, Ph<sub>2</sub>PH•BH<sub>3</sub> avoids the problem of phosphine oxidation by protecting the phosphine from oxidation and is available through chemical vendors.<ref name = piotrowski/><br />
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==References==<br />
{{reflist}}<br />
<br />
[[Category:Aromatic compounds]]<br />
[[Category:Phosphines]]</div>159.178.113.190