1,5-Diaminonaphthalene

1,5-Diaminonaphthalene is an organic compound with the formula CH. It is one of several diaminonaphthalenes. It is a colorless solid that darkens in air due to oxidation.

Synthesis and reactions

It is prepared by reduction of 1,5-dinitronaphthalene, which in turn is obtained with the 1,8-isomers by nitration of 1-nitronaphthalene. It can also be prepared by treatment of 1,5-dihydroxynaphthalene with ammonium sulfite. It is a precursor to naphthalene-1,5-diisocyanate, a precursor to specialty polyurethanes.
1,5-Diaminonaphthalene is a precursor imine-linked covalent organic frameworks.

Analytical matrix for MALDI/LDI. 1,5-Diaminonaphthalene is used as a low-background matrix for MALDI mass spectrometry, including mass spectrometry imaging of small molecules in tissue sections. It has also been reported as a highly performing electron-transfer matrix for LDI analyses of low-mass species.
Precursor to naphthalene-1,5-diisocyanate. 1,5-Diaminonaphthalene is an industrial intermediate to diisocyanates, notably naphthalene-1,5-diisocyanate, which is used to make high-performance polyurethane elastomers.