|
|Section2= |Section7= }} 3,3'-Diaminobenzidine (DAB) is an organic compound that is both chemically and thermodynamically stable. This derivative of benzidine is a precursor to polybenzimidazole fiber. This fiber can be used to construct materials that are resistant to chemicals and high temperature. Fabrics made from these fibers do not melt when exposed to flame and do not burn.〔Hans Schwenecke, Dieter Mayer "Benzidine and Benzidine Derivatives" in ''Ullmann’s Encyclopedia of Industrial Chemistry'', 2005, Wiley-VCH, Weinheim.〕 As its water-soluble tetrahydrochloride, DAB has been used in immunohistochemical staining of nucleic acids and proteins. DAB is symmetric about the central carbon bond between both ring structures. In the crystal, the rings of each molecule are co-planar and the amine units connect molecules to form an intermolecular 3-dimensional hydrogen bond network. ==Preparation== Diaminobenzidine, which is commercially available, is prepared by reacting 3,3'-dichlorobenzidine and ammonia with a copper catalyst at high temperature and pressure, followed by acidic workup. An alternate synthesis route involves the diacylation of benzidine with acetic anhydride under basic conditions:〔 :(NH2)C6H4C6H4(NH2) + 2(CH3CO)2O ⟶ (NHCOCH3)C6H4C6H4(NHCOCH3) + 2CH3CO2H The diacetylated compound then undergoes nitration with nitric acid to produce an ortho-dinitro compound due to the ortho-directing acetyl substituents:〔 :(NHCOCH3)C6H4C6H4(NHCOCH3) + 2HNO3 ⟶ (O2N)(NHCOCH3)C6H3C6H3(NHCOCH3)(NO2) + 2H2O The acetyl groups are then removed through saponification:〔 :(O2N)(NHCOCH3)C6H3C6H3(NHCOCH3)(NO2) + 2NaOH ⟶ (O2N)(NH2)C6H3C6H3(NH2)(NO2) + 2(NaOCOCH3) The dinitrobenzidine compound is then reduced with hydrochloric acid and iron as a catalyst to produce 3,3'-diaminobenzidine:〔 :3(O2N)(NH2)C6H3C6H3(NH2)(NO2) + 12HCl + 10Fe0 ⟶ 3(NH2)2C6H3C6H3(NH2)2 + 4Fe2O3 + 6FeCl2 The reduction of the dinitrobenzidine compound can also proceed with tin(II) chloride instead of iron powder or with sodium dithionite in methanol.〔 抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)』 ■ウィキペディアで「3,3'-Diaminobenzidine」の詳細全文を読む スポンサード リンク
|