查看“︁邻二氮菲”︁的源代码

{{Chembox
|   Name = 邻二氮菲
|   ImageFile = 1,10-phenanthroline.svg
<!-- | ImageSize = 200px -->
|   ImageName = 1,10-邻二氮菲
|   ImageFile1 = Phenanthroline.JPG
|   ImageName1 = 邻二氮菲一水合物
|   IUPACName = 1,10-phenanthroline
|   OtherNames = 邻菲罗啉、邻菲啰啉、<br />邻二氮杂菲、邻菲咯啉、<br />1,10-菲啰啉
|   Abbreviation = phen
| Section1 = {{Chembox Identifiers
| CASNo = 66-71-7
| CASNo_Comment = 无水
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo2 = 5144-89-8
| CASNo2_Comment = 一水
| CASNo2_Ref = {{cascite|correct|CAS}}
|    SMILES  =  c1ccnc3c1ccc2cccnc23
|    RTECS  =  SF8300000
|  ChemSpiderID_Ref  = {{chemspidercite|correct|chemspider}}|  ChemSpiderID  =  1278
|  InChI  =  1/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H
|  InChIKey  =  DGEZNRSVGBDHLK-UHFFFAOYAW
|  ChEMBL_Ref  = {{ebicite|correct|EBI}}|  ChEMBL  =  415879
|  StdInChI_Ref  = {{stdinchicite|correct|chemspider}}|  StdInChI  =  1S/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H
|  StdInChIKey_Ref  = {{stdinchicite|correct|chemspider}}|  StdInChIKey  =  DGEZNRSVGBDHLK-UHFFFAOYSA-N
|  DrugBank_Ref  = {{drugbankcite|correct|drugbank}}|  DrugBank  =  DB02365
|  ChEBI_Ref  = {{ebicite|correct|EBI}}|  ChEBI  =  44975

}}
| Section2 = {{Chembox Properties
|   Formula = C<sub>12</sub>H<sub>8</sub>N<sub>2</sub>
|   MolarMass = 180.3 
|   Appearance = 无色晶体
|   Density = 
|   Solubility = 中度可溶
|   Solvent = 其他溶剂
|   SolubleOther = 可溶于[[丙酮]]、[[乙醇]]、[[苯]]，不溶于[[石油醚]]
|   MeltingPt = 117 °C
|   BoilingPt =
|   pKb = 
  }}
| Section7 = {{Chembox Hazards
|   ExternalMSDS =
|   MainHazards = 具有中度的神经毒性，强肾毒性和利尿作用
|   RPhrases = {{R25}}, {{R50/53}}
|   SPhrases = {{S45}},{{S60}},{{S61}}
  }}
| Section8 = {{Chembox Related
|   OtherCpds = [[2,2'-联吡啶]]、[[菲]]、<br />[[邻二氮菲亚铁离子]]
  }}
}}

'''邻二氮菲'''，即“1,10-邻二氮杂[[菲]]”，也称'''邻菲罗啉'''、'''邻菲啰啉'''、'''邻菲咯啉'''，是一种常用的[[氧化还原指示剂]]。它是一个[[齿合度|双齿]][[杂环化合物]][[配体 (化学)|配体]]，类似于[[2,2'-联吡啶]]，会与大多数[[金属]][[离子]]形成很稳定的[[配合物]]。<ref>{{cite journal | title = Resolution of the tris-(1,10-Phenanthroline)Nickel(II) Ion | author = [[George B. Kauffman]], Lloyd T. Takahashi | journal = [[Inorg. Synth.]] | year = 1966 | volume = 5 | pages = 227–232}}</ref><ref>{{cite journal | author =F. P. Dwyer, E. C. Gyarfas, W. P. Rogers, J. H. Koch | title = Biological Activity of Complex Ions | url =https://archive.org/details/sim_nature-uk_1952-08-02_170_4318/page/n19 | journal = [[Nature (journal)|Nature]] | volume = 170 | pages = 190–191 | year = 1952 | doi = 10.1038/170190a0}}</ref>

邻二氮菲最常用的应用是[[分光光度法]]测定[[铁]]。它可通过[[邻苯二胺]]、[[硫酸]]、[[甘油]]和[[砷酸]]的水溶液回流反应制取。<ref>{{cite journal | author = B. E. Halcrow, W. O. Kermack | journal = [[J. Chem. Soc.]] | pages = 155–157 | year = 1946 | doi = 10.1039/jr9460000155 | title = 43. Attempts to find new antimalarials. Part XXIV. Derivatives of o-phenanthroline (7 : 8 : 3′ : 2′-pyridoquinoline)}}</ref>

邻二氮菲在[[pH]]为2~9时，会与[[亚铁离子]]（Fe<sup>2+</sup>）形成稳定的[[橙红色]][[邻二氮菲亚铁离子]]（[Fe(phen)<sub>3</sub>]<sup>2+</sup>），可通过[[分光光度法]]来分析。<ref>Belcher, R. "Application of chelate Compounds in Analytical Chemistry" Pure and Applied Chemistry, 1973, volume 34, pages 13-27.</ref>logK=21.3，[[摩尔吸收系数]]为1.1×10<sup>4</sup>，最大吸收峰在508nm。该法选择性高。氧化型[Fe(phen)<sub>3</sub>]<sup>3+</sup>显浅蓝色，[[半反应]]为：
:<math>Fe(C_{12} H_8 N_2)_3^{3+} + e^{-} \leftrightharpoons Fe(C_{12} H_8 N_2)_3^{2+}</math>
:::<math>[H^{+}] = 1 mol/L, E^{\ominus} = 1.06 V</math>

邻二氮菲-Fe(II)指示剂可通过将1.485g一水合邻二氮菲和0.695g[[硫酸亚铁|FeSO<sub>4</sub>·7H<sub>2</sub>O]]溶于100mL水中来配制。用于[[硫酸鈰(Ⅳ)]]滴定铁盐的指示剂。一个相关的配体是[[红菲绕啉]]（BPT），4,7-二苯基-1,10-邻二氮菲。[https://web.archive.org/web/20080519045545/http://www.dojindo.cn/productd.asp?pd=18]

邻二氮菲也可用于[[有机锂试剂|烷基锂化合物]]含量的分析。具体步骤是使样品与少量（约1mg）的邻二氮菲作用，呈深色，再用[[醇]]类滴定，直到达到无色的滴定终点。<ref>{{OrgSynth | author = Paul J. Fagan and William A. Nugent | title = 1-Phenyl-2,3,4,5-Tetramethylphosphole| collvol = 9 | collvolpages = 653| year = 1998 | prep = CV9P0653}}</ref>

==参见==
*[[二苯胺磺酸钠]]

==参考资料==
<div class="references-small">
<references/>
</div>

==外部链接==
*[http://202.113.22.23/fxhx/WSJX/GDFX/gdfx-2.htm 邻二氮菲分光光度法测定铁] {{Wayback|url=http://202.113.22.23/fxhx/WSJX/GDFX/gdfx-2.htm |date=20100409011335 }}

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[[Category:氧化还原指示剂]]
[[Category:螯合配体]]
[[Category:邻二氮菲| ]]