查看“︁二苯胺”︁的源代码

{{distinguish|二氨基苯}}
{{Chembox
| Name = 二苯胺
| NameEn = Diphenylamine
| ImageFile = Diphenylamine 200.svg
| ImageSize = 
| ImageFile2 = Diphenylamine sample.jpg
| IUPACName = 
| IUPACNameZh = 
| OtherNames = 
| Section1 = {{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4640
| SMILES = c1ccc(cc1)Nc2ccccc2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 11003
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9N3CBB0BIQ
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C11016
| InChI = 1/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
| InChIKey = DMBHHRLKUKUOEG-UHFFFAOYAJ
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 38688
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DMBHHRLKUKUOEG-UHFFFAOYSA-N
| Abbreviations = DPA
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 122-39-4
| RTECS = 9
}}
| Section2 = {{Chembox Properties
|   Formula = C<sub>12</sub>H<sub>11</sub>N 
|   MolarMass = 169.23 
|   Appearance = 白色结晶
|   Density = 1.2 g/cm³
|   MeltingPt = 53
|   Melting_notes =
|   BoilingPt = 302
|   Boiling_notes = 
|   Solubility = 微溶
|   SolubleOther = 
|   Solvent = 
|   pKa = 
|   pKb = }}
| Section7 = {{Chembox Hazards
|   EUClass = 
|   EUIndex = 
|   MainHazards = 有毒，可能有致癌性<br />和致诱变性
|   NFPA-H = 3
|   NFPA-F = 1
|   NFPA-R = 0
|   NFPA-O =
|   RPhrases = {{R23}}, {{R24}}, {{R25}}, {{R33}}, {{R50}}, {{R53}}
|   SPhrases = {{S36}}, {{S37}}, {{S45}}, {{S60}}, {{S61}}
|   RSPhrases =
|   FlashPt = 152
|   Autoignition = 
|   ExploLimits = 
|   PEL = }}
}}

'''二苯胺'''，化学式(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>NH，纯品为白色单斜片状结晶，但常因氧化而发黄。<ref name=Ullmann>P. F. Vogt, J. J. Gerulis, “Amines, Aromatic” in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim.</ref>有毒。

==制备==
通过[[苯胺]]在加热和氧化物催化下，缩合放出[[氨]]制备：
:<chem>2 C6H5NH2 -> (C6H5)2NH + NH3</chem>

==性质==
白色单斜片状结晶，易溶于[[苯]]、[[丙酮]]、[[四氯化碳]]和[[乙酸乙酯]]，溶于[[乙醚]]、[[乙醇]]、[[石油醚]]和[[冰醋酸]]。有[[弱碱]]性，与[[强酸]]作用生成可溶于水的[[盐 (化学)|盐]]。''K''<sub>b</sub>值为10<sup>-14</sup>。

==用途==
在橡胶和水果工业<ref>W. J. Bramlage. (University of Massachusetts Department of Plant and Soil Sciences). "[http://postharvest.tfrec.wsu.edu/pgDisplay.php?article=N6I2C Apple Scald, a Complex Problem] {{Wayback|url=http://postharvest.tfrec.wsu.edu/pgDisplay.php?article=N6I2C |date=20090315090439 }}". ''Post Harvest Pomology Newsletter'', 6(2): 11-14
September 1988.</ref>中用作[[抗氧化剂]]。也用作染料中间体。与[[硫]]反应，环化为[[吩噻嗪]]，后者是很多药物的合成前体：<ref>T. Kahl, K.-W. Schröder, F. R. Lawrence, W. J. Marshall, Hartmut Höke, Rudolf Jäckh, "Aniline" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH: Weinheim.</ref>
:<chem>(C6H5)2NH + 2 S -> S(C6H4)2NH + H2S</chem>

与[[碘]]作用，环化为[[咔唑]]：
:<chem>(C6H5)2NH + I2 -> (C6H4)2NH + 2 HI</chem>

与[[碘苯]]偶联，生成[[三苯胺]]。<ref>{{OrgSynth | author = F. D. Hager| title = Triphenylamine| collvol = 1 | collvolpages = 544 | year = 1941 | prep = CV1P0544}}</ref>

二苯胺也是用于检验[[DNA]]的试剂。它与DNA水浴加热生成蓝色物质。（参见[[DNA提取]]）

==参见==
*[[二氨基苯]]
*[[联苯胺]]、[[联苯胺重排反应]]

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

==外部链接==
*{{ICSC|0466|04}}

[[Category:芳香胺]]
[[Category:二苯氨基化合物]]