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benzenediazonium chloride : ウィキペディア英語版
benzenediazonium chloride

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Benzenediazonium chloride is an organic compound with the formula ()Cl. It is a salt of a diazonium cation and chloride. It exists as a colourless solid that is soluble in polar solvents including water. It is the parent member of the aryldiazonium compounds, which are widely used in organic chemistry. Because the salt is unstable, it is not commercially available but is prepared upon demand.
== Synthesis ==
This compound is prepared by diazotization of aniline.〔 The procedure described the tetrafluoroborate salt of phenyldiazonium.〕 The conversion involves in situ production of nitrous acid (HNO2), which reacts with the aniline:
: C6H5NH2 + HNO2 + HCl → ()Cl + 2 H2O
The reactions are conducted at low temperature to minimize decomposition of the diazonium salt.
Diazonium chloride can also be prepared by treating nitrite esters with aniline in presence of HCl. Nitrite esters are formed from alcohol and nitrous acid.
: C5H11ONO + HCl + C6H5NH2 → ()Cl + C5H11OH + H2O

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