| Identification | More | [Name]
Diaminomaleonitrile | [CAS]
1187-42-4 | [Synonyms]
1,2-DIAMINO-1,2-DICYANOETHYLENE
CIS-2,3-DIAMINOBUT-2-ENEDINITRILE
DAMN
DIAMINOMALEIC ACID DINITRILE
DIAMINOMALEONITRILE
TIMTEC-BB SBB009976
2,3-diamino-,(Z)-2-Butenedinitrile
2,3-diamino-2-butenedinitrile
3-diamino-(z)-2-butenedinitril
diaminoaleo dinitrile
2-Butenedinitrile, 2,3-diamino-, (2Z)-
2,3-Diaminomaleodinitrile
(Z)-2,3-Diaminobut-2-enedinitrile
2-Butenedinitrile, 2,3-diamino-, (Z)-
(Z)-2,3-Diamino-2-butenedinitrile
Hydrogen cyanide tetramer | [EINECS(EC#)]
214-697-6 | [Molecular Formula]
C4H4N4 | [MDL Number]
MFCD00001870 | [Molecular Weight]
108.1 | [MOL File]
1187-42-4.mol |
| Chemical Properties | Back Directory | [Appearance]
brown crystalline powder | [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 | [form ]
Crystalline Powder | [pka]
-2.77±0.70(Predicted) | [color ]
Brown | [Water Solubility ]
5 g/L (25 ºC) | [Sensitive ]
Light Sensitive | [BRN ]
878333 | [Exposure limits]
NIOSH: IDLH 25 mg/m3 | [InChI]
1S/C4H4N4/c5-1-3(7)4(8)2-6/h7-8H2/b4-3- | [InChIKey]
DPZSNGJNFHWQDC-ARJAWSKDSA-N | [SMILES]
N\C(C#N)=C(/N)C#N | [CAS DataBase Reference]
1187-42-4(CAS DataBase Reference) | [EPA Substance Registry System]
1187-42-4(EPA Substance) |
| Questions And Answer | Back Directory | [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.
|
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302+H312+H332 | [Precautionary statements ]
P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312 | [Hazard Codes ]
Xn,T | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R25:Toxic if swallowed. | [Safety Statements ]
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 3439 6.1/PG 3
| [WGK Germany ]
3
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29269095 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Acetone cyanohydrin | [Preparation Products]
1-Methyl-1H-imidazole-5-carbonyl chloride hydrochloride-->1-Methyl-1H-imidazole-4-carboxylic acid-->Imidazole-4-methanol-->4,5-Imidazoledicarboxylic acid-->1-Methyl-1H-imidazole-5-carboxylic acid-->1-Methyl-1H-imidazol-5-yl isocyanate-->4,5-Dicarboxy-1-methyl-1H-imidazole-->1H-Imidazole-4-carboxylic acid-->1-Methyl-1H-imidazole-4,5-dicarbonitrile-->4,5-Dicyanoimidazole-->Ethyl N-(2-amino-1,2-dicyanovinyl)iminoformate-->1H-1,2,3-triazole-4,5-dicarbonitrile-->1,2-Dimethyl-1H-Imidazole-4,5-Dicarbonitrile |
| Hazard Information | Back Directory | [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]
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 |
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| Company Name: |
J & K SCIENTIFIC LTD.
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| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
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| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
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| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
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