Overview
The importance of diaminomaleonitrile (DAMN) as a readily available and cheap building block for the synthesis of various nitrogen heterocycles has attracted the attention of organic chemists worldwide. An enormous number of research studies have focused on the preparation of various heterocycles that play a role in the pharmaceutical, cosmetics, dyes, and pigment industries, among others. This review details developments in the chemistry and reactions of DAMN over the last decade including novel methods utilised, new compounds prepared, and significant applications.
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.
Solubility Information
Solubility in water: 5g/L (25°C). Other solubilities: soluble in methanol, ethanol, dmf and dimethyl, sulfoxide, slightly soluble in ethyl ether and dioxane, insol. in benzene,acetone,xylene,toluene and cs2.
USES
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.
Chemical Properties
brown crystalline powder
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.
Preparation
Diaminomaleonitrile is obtained by tetramerization of hydrocyanic acid in the presence of catalysts such as alkylaluminum compounds.
Synthesis Reference(s)
The Journal of Organic Chemistry, 37, p. 4133, 1972
DOI: 10.1021/jo00798a037
General Description
Brown powder.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Diaminomaleonitrile is sensitive to prolonged exposure to air.
Fire Hazard
Flash point data are not available for Diaminomaleonitrile, but Diaminomaleonitrile is probably combustible.
Solubility in organics
They are soluble in methanol, ethanol, and N,N-dimethylformamide; slightly soluble in water and dioxane; and insoluble in acetone, benzene, xylene, and carbon disulfifide.
