89418-04-2

Basic information

• Product Name: Acetamide, N-(2-amino-1,2-dicyanovinyl)- (6CI,7CI)
• Synonyms: Acetamide, N-(2-amino-1,2-dicyanovinyl)- (6CI,7CI)
• CAS NO: 89418-04-2
• Molecular Formula: C6H6N4O
• Molecular Weight: 150.14
• Mol File: 89418-04-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Acetamide, N-(2-amino-1,2-dicyanovinyl)- (6CI,7CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Acetamide, N-(2-amino-1,2-dicyanovinyl)- (6CI,7CI)(89418-04-2)
• EPA Substance Registry System: Acetamide, N-(2-amino-1,2-dicyanovinyl)- (6CI,7CI)(89418-04-2)

Safety Data

• Hazardous Substances Data: 89418-04-2(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 1187-42-4 diaminomaleonitrile 
• 75-36-5 acetyl chloride 
• 65604-69-5 N-((Z)-2-amino-1,2-dicyanoethenyl)acetamide 

Downstream Products

• 100382-42-1 acetylamino-((Ξ)-benzylidenamino)-maleonitrile 

Relevant articles and documents

The enhancement of the D-A effect of an asymmetric Schiff base by introducing acetyl groups into diaminomaleonitrile: Synthesis, red fluorescence and crystal structure

An asymmetrical salen-type organic ligand was designed and synthesized by a new strategy developed using a precursor Ac-DMN, which is a diaminomaleonitrile (DMN) incorporated with an acetyl group. In this study, two types of asymmetrical ligands, namely Ac-DMN-salicylaldehyde (L0) and Ac-DMN-4-N,N-diethyl-salicylaldehyde (L1), and their Zn(ii) coordination complexes were studied. With the electron-pushing substituent, L1 showed interesting photoluminescence behaviour distinct from that of L0. In a THF solution, the maximum fluorescence emission of L1 red-shifted to 90 nm compared with that of L0. Furthermore, in a THF-H2O solution, L1 exhibited aggregation-induced emission (AIE), but L0 exhibited aggregation-caused quenching (ACQ). Upon coordination with Zn(ii), the maximum emission wavelengths in THF for both the ligands were red-shifted to 100 nm and 105 nm, respectively. The crystalline solid-state photoluminescence properties were studied based on the single-crystal structural analysis.

Novel 2H-1,2,3-Triazole sodium complex from N-[2-amino-1,2-dicyanovinyl]alkanamides

Diazotization at 0 °C of N-[2-amino-1,2-dicyanovinyl]ethanamide 2a or propanamide 2b prepared from diaminomaleonitrile (DAMN) 1 using aqueous acetic acid and NaNO2 solution furnished sodium complex 3. The X-ray structure of the complex 3 showed that it is a 1:1 mixture of the neutral 2H-triazole heterocycle 4ii and its anion deprotonated at the central (N) atom of the ring, together with a sodium counter ion and two coordinated water molecules. However, when the diazotization reaction was carried out in the presence of aqueous HCl, the product was 5-cyano-2H-[1,2,3]triazole-4-carboxylic acid amide monohydrate 4ii. Diazotization of DAMN 1 using aqueous HCl furnished 1H-1,2,3-triazole-4,5-dicarbonitrile 5, whereas with acetic acid there was no reaction, and hence no route analogous to that leading to complex 3. The structure of both complex 3 and the triazole monohydrate 4ii were solved using X-ray crystallography, and the compounds under study were fully characterized using spectroscopic techniques.

Synthesis of novel 5-amino-6-ethoxy-2-alkylpyrimidine-4-carbonitriles

The synthesis of highly functionlized 5-amino-6-ethoxy-2-alkylpyrimidine-4-carbonitriles under acid catalysis conditions was studied. The synthesis was performed by refluxing the N-(2-ammonio-1,2-dicyanovinyl)alkylamide chloride as N-(2-amino-1,2-dicyanovinyl)acetamide in ethanol. Pyrimidine formation implied rotation around the C1-C2 double bond of the salt at some stage of the reaction. The results showed that the imidoyl chloride was a critical intermediate in the reaction and the use of other acid catalysts gave only traces of 5-amino-6-ethoxy-2-alkylpyrimidine-4-carbonitriles.