1,8-Diaminonaphthalene Explained

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.^[1]

Synthesis and reactions

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.^[2] 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.^[3]

See also

• C₁₀H₁₀N₂

Notes and References

1. .
2. 10.1021/ol201973w. Green Synthesis of Polycyclic Benzimidazole Derivatives and Organic Semiconductors. 2011. Mamada. Masashi. PéRez-BolíVar. César. Anzenbacher. Pavel. Organic Letters. 13. 18. 4882–4885. 21863817. 32185653 .
3. F.K. Behbahani, F.M.Golchin. 10.1016/j.jtusci.2015.10.004. A new catalyst for the synthesis of 2-substituted perimidines catalysed by FePO4. Journal of Taibah University for Science. 2017. 11. 1 . 85–89. 98648448. free. 2017JTUS...11...85B .