1187-42-4

Raw materials And Preparation Products

Hazard Information

General Description

Brown powder.

Reactivity Profile

DIAMINOMALEONITRILE(1187-42-4) is sensitive to prolonged exposure to air.

Air & Water Reactions

Insoluble in water.

Fire Hazard

Flash point data are not available for this compound, but DIAMINOMALEONITRILE is probably combustible.

Chemical Properties

brown crystalline powder

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

Synthesis

75-86-5

1187-42-4

In an autoclave, 10 g of sodium cyanide (NaCN) was added to 130 ml of acetone cyanohydrin. Subsequently 6.54 g of methyl mercaptan (CH3SH) was added. The reaction mixture was stirred at 60°C for 2 h. It was observed that the color of the solution changed to orange. After completion of the reaction, the excess acetone cyanohydrin was neutralized by addition of sodium carbonate (Na2CO3). The reaction solution was filtered and the filtrate was subsequently evaporated to give the orange solid product diaminomaleonitrile (recovery 33.7 g, 88% yield).

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.

References

[1] Patent: US2015/197487, 2015, A1. Location in patent: Paragraph 0029

Material Safety Data Sheet(MSDS)

Questions And Answer

• 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.

  ;

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

Related Products