邻二氮菲

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邻二氮菲



IUPAC名
1,10-phenanthroline
别名
邻菲罗啉、邻菲啰啉、
邻二氮杂菲、邻菲咯啉、
1,10-菲啰啉
识别

CAS号

66-71-7（无水）  ✓
5144-89-8（一水）  ✓

ChemSpider

1278

SMILES



InChI



InChIKey

DGEZNRSVGBDHLK-UHFFFAOYAW

ChEBI

44975

RTECS
SF8300000

DrugBank

DB02365
性质

化学式

C12H8N2

摩尔质量
180.3 g·mol⁻¹
外观
无色晶体

熔点
117 °C

溶解性（水）
中度可溶

溶解性（其他溶剂）
可溶于丙酮、乙醇、苯，不溶于石油醚
危险性

警示术语
R：R25, R50/53

安全术语
S：S45,S60,S61
主要危害
具有中度的神经毒性，强肾毒性和利尿作用
相关物质
相关化学品

2,2'-联吡啶、菲、
邻二氮菲亚铁离子
若非注明，所有数据均出自一般条件（25 ℃，100 kPa）下。

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。它是一个双齿杂环化合物配体，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。[1][2]


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。[3]


邻二氮菲在pH为2~9时，会与亚铁离子（Fe2+）形成稳定的橙红色邻二氮菲亚铁离子（[Fe(phen)3]2+），可通过分光光度法来分析。[4]logK=21.3，摩尔吸收系数为1.1×104，最大吸收峰在508nm。该法选择性高。氧化型[Fe(phen)3]3+显浅蓝色，半反应为：



Fe(C12H8N2)33++e−⇋Fe(C12H8N2)32+displaystyle Fe(C_12H_8N_2)_3^3++e^-leftrightharpoons Fe(C_12H_8N_2)_3^2+displaystyle Fe(C_12H_8N_2)_3^3++e^-leftrightharpoons Fe(C_12H_8N_2)_3^2+
[H+]=1mol/L,E⊖=1.06Vdisplaystyle [H^+]=1mol/L,E^ominus =1.06Vdisplaystyle [H^+]=1mol/L,E^ominus =1.06V

邻二氮菲-Fe(II)指示剂可通过将1.485g一水合邻二氮菲和0.695gFeSO4·7H2O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。[1]


邻二氮菲也可用于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。[5]



参见


  • 二苯胺磺酸钠


参考资料




  1. ^ George B. Kauffman, Lloyd T. Takahashi. Resolution of the tris-(1,10-Phenanthroline)Nickel(II) Ion. Inorg. Synth. 1966, 5: 227–232. 


  2. ^ F. P. Dwyer, E. C. Gyarfas, W. P. Rogers, J. H. Koch. Biological Activity of Complex Ions. Nature. 1952, 170: 190–191. doi:10.1038/170190a0. 


  3. ^ B. E. Halcrow, W. O. Kermack. 43. Attempts to find new antimalarials. Part XXIV. Derivatives of o-phenanthroline (7 : 8 : 3′ : 2′-pyridoquinoline). J. Chem. Soc. 1946: 155–157. doi:10.1039/jr9460000155. 


  4. ^ Belcher, R. "Application of chelate Compounds in Analytical Chemistry" Pure and Applied Chemistry, 1973, volume 34, pages 13-27.


  5. ^ Paul J. Fagan and William A. Nugent (1998). "1-Phenyl-2,3,4,5-Tetramethylphosphole". Org. Synth.; Coll. Vol. 9: 653. 



外部链接



  • 邻二氮菲分光光度法测定铁[永久失效連結]
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