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Benzenediazonium chloride

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colorless crystals

Benzenediazonium chloride Synthesis of BENZENEDIAZONIUM CHLORIDE PrepChemcom

Reactions with benzenediazonium chloride


Benzenediazonium chloride is an organic compound with the formula [C6H5N2]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.

Contents

Benzenediazonium chloride Synthesis of BENZENEDIAZONIUM CHLORIDE PrepChemcom

Formation of benzenediazonium chloride


Synthesis

Benzenediazonium chloride Chapter 3 Example

This compound is prepared by diazotization of aniline. The conversion involves in situ production of nitrous acid (HNO2), which reacts with the aniline:

C6H5NH2 + HNO2 + HCl → [C6H5N2]Cl + 2 H2O

The reactions are conducted at low temperature to minimize decomposition of the diazonium salt.

Benzenediazonium chloride wwwchemspidercomImagesHandlerashxid54953ampw2

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 → [C6H5N2]Cl + C5H11OH + H2O

Chemical properties

The diazo group (N2) can be replaced by many other groups, usually anions, giving a variety of substituted phenyl derivatives:

C6H5N2+ + Nu → C6H5Nu + N2

These transformations are associated with many named reactions including the Schiemann reaction, Sandmeyer reaction, and Gomberg-Bachmann reaction. A wide range of groups that can be used to replace N2 including halide, SH, CO2H, OH. Of considerable practical value in the dye industry are the diazo coupling reactions.

Safety

The compound is explosive.

References

Benzenediazonium chloride Wikipedia


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