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N,N-Dimethylphenylenediamine

N,N-Dimethylphenylenediamine

N,N-Dimethylphenylenediamine (dimethyl-4-phenylenediamine) is an organic compound with the formula . It is one of the phenylenediamines, a class of compounds that have long attracted attention for their redox properties. This diamine is, for example, easily oxidized to a deep red radical cation, which is called Wurster's Red. The related Wurster's Blue cation has four N-methyl groups

Structure of Wurster's Red bromide with bond distances in picometers

Synthesis

Dimethyl-4-phenylenediamine is prepared by the nitration of dimethylaniline followed by reduction of the resulting 4-nitrodimethylaniline. A variety of methods have been examined.

Applications

Dimethyl-4-phenylenediamine can be converted to methylene blue by reaction with dimethylaniline and sodium thiosulfate in several steps:

:[[File:Synthesis_of_methylene_blue.png|600px]]

It reacts with carbon disulfide to give the corresponding mercaptobenzothiazole: :

History

Casmir Wurster discovered tetramethylphenylenediamine and its easy oxidation. Subsequent work revealed the variety of redox properties of the phenylenediamines.{{cite journal

References

References

  1. ''[[Merck Index]]'', 11th Edition, '''3242'''
  2. (1968). "The crystal structure of Würster's red bromide". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry.
  3. (2011). "Efficient and highly selective iron-catalyzed reduction of nitroarenes". Chemical Communications.
  4. Horst Berneth. (2012). "Azine Dyes". Wiley-VCH.
  5. (1879). "Ueber die Einwirkung oxydirender Agentien auf Tetramethylparaphenylendiamin". Berichte der Deutschen Chemischen Gesellschaft.
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4-aminophenyl-compounds diamines dimethylamino-compounds
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