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1,8-Diaminonaphthalene

1,8-Diaminonaphthalene

1,8-bis(dimethylamino)naphthalene

1,8-Diaminonaphthalene is an organic compound with the formula CH(NH). It is one of several isomeric naphthalenediamines. It is a colorless solid that darkens in air due to oxidation. It is a precursor to commercial pigments.

Synthesis and reactions

Chemical structure of 12-phthaloperinone, a derivative of 1,8-diaminonaphthalene

It is prepared by reduction of 1,8-dinitronaphthalene, which in turn is obtained as a mixture of isomers by nitration of 1-nitronaphthalene.

Upon treatment with phthalic anhydride derivatives, the diamine converts to phthaloperinones. The derivative from phthalic anhydride itself, Solvent Orange 60, is a useful orange pigment. It is a precursor to 1,8-bis(dimethylamino)naphthalene. This compound used to produce perimidines by various aldehydes.

References

References

  1. (2005). "Naphthalene Derivatives".
  2. (2011). "Green Synthesis of Polycyclic Benzimidazole Derivatives and Organic Semiconductors". Organic Letters.
  3. F.K. Behbahani, F.M.Golchin. (2017). "A new catalyst for the synthesis of 2-substituted perimidines catalysed by FePO4". Journal of Taibah University for Science.
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