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Uses of Diaminomaleonitrile

Aug 22，2022

Diaminomaleonitrile (DAMN) is an organic compound composed of two amino groups and two nitrile groups bonded to a central alkene unit. The systematic name reflects its relationship to maleic acid.

The chemical can be formed by polymerization of hydrogen cyanide and can be used as the starting point for the synthesis of several classes of heterocyclic compounds. Therefore, it has been considered as a possible organic chemical present in prebiotic conditions.

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Uses

Diaminomaleonitrile is a reagent used for the synthesis of 1,4-diazepine-2,3-dicarbonitrile dervatives. Also, it is used for the synthesis of Diaminomaleonitrile-based Schiff bases with a donor-acceptor structure and an aggregation-enhanced emission feature.

Role in abiogenesis

Diaminomaleonitrile has been proposed since the 1960s as a key substance for the prebiotic synthesis of nucleobases. Photochemical rearrangement of DAMN under UV light gives 4-aminoimidazole-5-carbonitrile (AICN), which can react further to form various nucleobases.

Early experiments have also suggested that certain amino acids, such as aspartic acid, alanine, and glycine, may have their probiotic origins in the acidic hydrolysis of diaminomaleonitrile.

Due to the ubiquity of hydrogen cyanide and its oligomers in space, it has been proposed that the dark material found in comets may consist of diaminomaleonitrile and higher oligomers, and that such polymers of HCN may have covered the surface of the early Earth.

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