Synthetic Uses of Aryl Diazonium Salts
- S-3-PHARMACEUTICAL-ORGANIC-CHEMISTRY
- Feb 28
- 1 min read
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Aryl diazonium salts (Ar-N₂⁺X⁻) are versatile intermediates in organic synthesis, particularly in the synthesis of aromatic compounds.
Key Reactions of Aryl Diazonium Salts
Sandmeyer Reaction
Aryl diazonium salts can be converted to aryl halides (Ar-Cl, Ar-Br, Ar-CN) by treating them with corresponding copper(I) salts like CuCl, CuBr, or CuCN.
This reaction is useful for introducing halogens or cyano groups into the aromatic ring.
Gattermann Reaction
Similar to the Sandmeyer reaction, but specifically used to introduce a formyl group (-CHO) into the aromatic ring.
Diazo Coupling
Aryl diazonium salts react with phenols or aromatic amines to form azo compounds (Ar-N=N-Ar'), which are often brightly colored and used in dyes.
Reduction
Aryl diazonium salts can be reduced to the corresponding aryl hydrides (Ar-H) using hypophosphorous acid (H₃PO₂) or other reducing agents.
Schiemann Reaction
Aryl diazonium salts can be fluorinated to form aryl fluorides (Ar-F) by treating with fluoroboric acid (HBF₄), followed by thermal decomposition.
Replacement by Hydroxyl Group
Aryl diazonium salts can be hydrolyzed to phenols (Ar-OH) by heating with water.
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