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benzidine : ウィキペディア英語版
benzidine

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Benzidine (trivial name), also called 1,1'-biphenyl-4,4'-diamine (systematic name), is the organic compound with the formula (C6H4NH2)2. it is an aromatic amine. It is a component of a test for cyanide. Related derivatives are used in the production of dyes. Benzidine has been linked to bladder and pancreatic cancer.〔(【引用サイトリンク】 Known and Probable Carcinogens )
==Synthesis and properties==
Benzidine is prepared in a two step process from nitrobenzene. First, the nitrobenzene is converted to 1,2-diphenylhydrazine, usually using iron powder as the reducing agent. Treatment of this hydrazine with mineral acids induces a rearrangement reaction to 4,4'-benzidine. Smaller amounts of other isomers are also formed. The benzidine rearrangement, which proceeds intramolecularly, is a classic mechanistic puzzle in organic chemistry.
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The conversion is described as a ()sigmatropic reaction.〔.〕
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In terms of its physical properties, 4,4'-benzidine is poorly soluble in cold water but can be recrystallized from hot water, where it crystallises as the monohydrate. It is dibasic, the deprotonated species has ''K''a values of 9.3 × 10−10 and 5.6 × 10−11. Its solutions react with oxidizing agents to give deeply coloured quinone-related derivatives.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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