查看“︁二苯基膦”︁的源代码

{{chembox
| verifiedrevid = 437791930
|   ImageFile = Diphenylphosphine.svg
|   ImageName = 球棒模型
|   ImageFile1 = Diphenylphosphine-3D-balls.png
|   ImageName1 = 球棒模型
|   ImageFile2 = Diphenylphosphine-3D-vdW.png
|   ImageSize2 = 200px
|   IUPACName= diphenylphosphane
| Section1 = {{Chembox Identifiers
|   ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 63209
| InChI = 1/C12H11P/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
| SMILES = c2c(Pc1ccccc1)cccc2
| InChIKey = GPAYUJZHTULNBE-UHFFFAOYAN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H11P/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GPAYUJZHTULNBE-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 829-85-6
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>12</sub>H<sub>11</sub>P
|   MolarMass = 186.19 
|   Appearance = 无色液体
|   Density = 1.07 g/cm<sup>3</sup>
|   Solubility =  不溶
|   BoilingPt = 280 °C (553 K)
  }}
| Section3 = {{Chembox Hazards
|   RPhrases = 17-36/37/38
|   SPhrases = 26-36
|   ExternalMSDS = [http://www.alfa.com/MSDSPDF/English_/56169.pdf External MSDS]
  }}
}}

'''二苯基膦'''是分子式为(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>PH的[[有机磷化学|有机磷化合物]]，是一种具有难闻气味的无色液体，在[[空气]]中容易被[[氧化]]，可以作为合成多种有机膦配体的前驱体。

== 合成方法 ==
二苯基膦可由廉价的[[三苯基膦]]通过锂化形成二苯基膦锂后用水淬灭制得：<ref>{{cite journal | author1 = Wittenberg, D. | author2 = Gilman, H. | authorlink2 = 亨利·吉尔曼 | title = Lithium Cleavages of Triphenyl Derivatives of Some Group Vb Elements in Tetrahydrofuran | journal = [[有机化学期刊|Journal of Organic Chemistry]] | year = 1958 | volume = 23 | issue = 7 | pages = 1063–1065 | doi = 10.1021/jo01101a613|url=http://pubs.acs.org/doi/abs/10.1021/jo01101a613 }}</ref>
:PPh<sub>3</sub>  +  2 Li   →   LiPPh<sub>2</sub>  +  LiPh
:LiPPh<sub>2</sub>  +  H<sub>2</sub>O   →   Ph<sub>2</sub>PH  +  LiOH

== 用途和反应 ==
二苯基膦是一种实验室中常见的中间体。通过去质子化可把它转变为二苯基膦化物：<ref name = piotrowski>{{ cite encyclopedia | author = Piotrowski, D. W.  | title = Diphenylphosphine | encyclopedia = Encyclopedia of Reagents for Organic Synthesis | publisher = [[約翰威立|John Wiley & Sons]] | location = New York | year = 2001 | doi = 10.1002/047084289X.rd427 }}</ref>
:Ph<sub>2</sub>PH + <sup>n</sup>BuLi   →   Ph<sub>2</sub>PLi + <sup>n</sup>BuH

诸如[[1,2-双(二苯基膦)乙烷]]和[[1,3-双(二苯基膦)丙烷]]之类的膦配体<ref>{{cite journal | journal = [[化学学会会刊|J. Chem. Soc.]] | year = 1962 | pages = 1490–1494 | doi = 10.1039/JR9620001490 | title = 283. The preparation of di- and tri-tertiary phosphines | author = W. Hewertson and H. R. Watson | url = http://pubs.rsc.org/en/Content/ArticleLanding/1962/JR/jr9620001490 | access-date = 2013-03-05 | archive-date = 2018-06-12 | archive-url = https://web.archive.org/web/20180612081039/http://pubs.rsc.org/en/Content/ArticleLanding/1962/JR/jr9620001490 | dead-url = no }}</ref><ref>{{cite journal|author=M. T. Honaker, B. J. Sandefur, J. L. Hargett, A. L. McDaniel, R. N. Salvatore|journal=[[四面体通讯|Tetrahedron Lett.]]|year=2003|volume=44|issue=46|pages=8373–8378|doi=10.1016/j.tetlet.2003.09.117|url=http://www.sciencedirect.com/science/article/pii/S0040403903022378|title=CsOH-promoted P-alkylation: a convenient and highly efficient synthesis of tertiary phosphines|access-date=2013-03-06|archive-date=2015-09-24|archive-url=https://web.archive.org/web/20150924160153/http://www.sciencedirect.com/science/article/pii/S0040403903022378|dead-url=no}}</ref>、[[Horner–Wadsworth–Emmons反应|维蒂希－霍纳尔试剂]]和[[季鏻盐]]的合成通常需要通过二苯基膦的烷基化来实现。二苯基膦或诸如二苯基膦钠和二苯基膦锂等二苯基膦化物作为亲核试剂能加成到碳杂原子双键上。比如在100°C的浓盐酸条件下，二苯基膦能加成到苯甲醛的醛基碳原子上：
:Ph<sub>2</sub>PH  +  PhCHO → Ph<sub>2</sub>P(O)CH<sub>2</sub>Ph

与叔膦相比，二苯基膦的碱性较弱。二苯基膦的共轭酸的pKa是0.03：<ref>{{cite journal|author=C. A. Streuli|title="Determination of Basicity of Substituted Phosphines by Nonaqueous Titrimetry"|journal=Analytical Chemistry|year=1960|volume=32|pages=985-987|doi=10.1021/ac60164a027|url=http://pubs.acs.org/doi/abs/10.1021/ac60164a027|access-date=2013-03-05|archive-date=2022-01-24|archive-url=https://web.archive.org/web/20220124125412/https://pubs.acs.org/doi/abs/10.1021/ac60164a027}}</ref>
:Ph<sub>2</sub>PH<sub>2</sub><sup>+</sup>    <math>\overrightarrow{\leftarrow}</math>   Ph<sub>2</sub>PH  +  H<sup>+</sup>

== 参考资料 ==
{{reflist}}

[[Category:磷-氢化合物]]
[[Category:二苯基膦基化合物]]