Diaminomaleonitrile Chemical Properties

Melting point:

178-179 °C (lit.)

Boiling point:

192.71°C (rough estimate)

Density 

1,36 g/cm³

refractive index 

1.6260 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

5000mg/l

pka

-2.77±0.70(Predicted)

form 

Crystalline Powder

color 

Brown

Water Solubility 

5 g/L (25 ºC)

Sensitive 

Light Sensitive

BRN 

878333

Exposure limits

NIOSH: IDLH 25 mg/m3

CAS DataBase Reference

1187-42-4(CAS DataBase Reference)

EPA Substance Registry System

Diaminomaleonitrile (1187-42-4)

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

20/21/22-25

Safety Statements 

36-24/25

RIDADR 

UN 3439 6.1/PG 3

WGK Germany 

3

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269095

MSDS

• Language:English Provider:Diaminomaleonitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Diaminomaleonitrile Usage And Synthesis

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.

Diaminomaleonitrile(1187-42-4)Related Product Information

• 2,3-DIAMINOTOLUENE
• Diaminomaleonitrile
• 2,3-Diaminomaleonitrile
• HYDROGEN CYANIDE
• 2-AMINO-1-(1-AZA-2-(5-CHLORO-2-HYDROXYPHENYL)VINYL)ETHENE-1,2-DICARBONITRILE
• N-(2-AMINO-1,2-DINITRILOVINYL)(PHENYLAMINO)FORMAMIDE
• 1,4,5,6-TETRAHYDRO-5,6-DIOXO-2,3-PYRAZINEDICARBONITRILE
• 2-AMINO-1-(1-AZA-4-(2-NITROPHENYL)BUTA-1,3-DIENYL)ETHENE-1,2-DICARBONITRILE
• 2-AMINO-1-(1-AZA-2-(3,5-DIBROMO-4-HYDROXYPHENYL)VINYL)ETHENE-1,2-DICARBONITRILE
• 2-AMINO-1-(1-AZA-2-(5-NITRO-2-(4-(TRIFLUOROMETHYL)PHENOXY)PHENYL)VINYL)ETHENE-1,2-DICARBONITRILE
• ETHYL N-(2-AMINO-1,2-DICYANOVINYL)IMINOFORMATE
• 2-AMINO-1-(1-AZA-2-(5-NITRO-2-(2-PYRIDYLTHIO)PHENYL)VINYL)ETHENE-1,2-DICARBONITRILE
• ((2-AMINO-1,2-DINITRILOVINYL)AMINO)-N-(3,4-DICHLOROPHENYL)FORMAMIDE
• 2,3-DICYANO-5,6-TETRAMETHYLENE-7-SPIRO-CYCLOHEXYLDIAZAPINE
• 2-AMINO-1-(1-AZA-2-(2-THIENYL)VINYL)ETHENE-1,2-DICARBONITRILE
• 2-AMINO-1-(1-AZA-2-(4-METHYLTHIOPHENYL)VINYL)ETHENE-1,2-DICARBONITRILE
• 2-AMINO-1-(1-AZA-2-(3,4-DIHYDROXYPHENYL)VINYL)ETHENE-1,2-DICARBONITRILE
• 2-AMINO-3-([(2,4-DICHLORO-1,3-THIAZOL-5-YL)METHYL]AMINO)BUT-2-ENEDINITRILE