156731-83-8

Basic information

• Product Name: 1H-Imidazole-4,5-dicarbonitrile,2-fluoro-1-methyl-(9CI)
• Synonyms: 1H-Imidazole-4,5-dicarbonitrile,2-fluoro-1-methyl-(9CI)
• CAS NO: 156731-83-8
• Molecular Formula: C₆H₃FN₄
• Molecular Weight: 150.1132232
• Product Categories: HALIDE
• Mol File: 156731-83-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Imidazole-4,5-dicarbonitrile,2-fluoro-1-methyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-4,5-dicarbonitrile,2-fluoro-1-methyl-(9CI)(156731-83-8)
• EPA Substance Registry System: 1H-Imidazole-4,5-dicarbonitrile,2-fluoro-1-methyl-(9CI)(156731-83-8)

Safety Data

• Hazardous Substances Data: 156731-83-8(Hazardous Substances Data)

Upstream product

• 115905-43-6 2-bromo-1-methyl-1H-imidazole-4,5-dicarbonitrile 

Relevant articles and documents

Synthesis, characterization, and thermolysis of C15N12

Synthesis of 1-methyl-2-fluoro-4,5-dicyanoimidazole was done by halogen exchange between 1-methyl-2-bromo-4,5-dicyanoimidazole and potassium fluoride. Halogen exchange between 1-methyl-2-bromo-4,5-dicyanoimidazole and lithium chloride in N-methylpyrrolidinone at 150 °C yielded 1-methyl-2-chloro-4,5-dicyanoimidazole, and additional heating to 210 °C resulted in the demethylation to yield 2-chloro-4,5-dicyanoimidazole. Thermolyses of the 2-halo-4,5-dicyanoimidazole derivatives (F, Cl) and 1-iodo-2-halo-4,5-dicyanoimidazole derivatives (Cl, Br, I) between 100 and 290 °C were found to yield Tris(imidazo)[1,2-α:1,2-c:1,2-e]-1,3,5-triazine-2,3,5,6,8,9- hexacarbonitrile, or HTT, with (C5N4)3 composition. HTT has been characterized and purified and the crystal structure obtained. Thermolysis of HTT at 490-500 °C gives a material with C/N = 1.020. The thermal properties of HTT and its decomposition products show thermal stability to 350 °C.

Synthesis and Characterization of Aromatic Secondary and Tertiary Amines and a New Imidazolone from Dicyanoimidazole

Aromatic primary amines substituted with electron donating groups such as methoxy and methyl at the para position undergo nucleophilic aromatic substitution (SNAr) reactions on 4,5-dicyano-2-fluoro-1-methylimidazole (2) in dimethyl sulfoxide at room temperature to give secondary amines substituted with dicyanoimidazolyl groups.Aromatic primary diamines and hydrazine similarly react with 2 to give new secondary diamines.Aromatic primary amines substituted with electron withdrawing group such as nitro group and also secondary amines such as carbazole react with 2 only after activation of the amine by deprotonation using sodium hydride.The electrophilicity of 2 is high enough to react with oxyanions such as nitrite and carbonate anions and also polar aprotic solvents via O-attack at 60 deg C to give a new imidazolone, 4,5-dicyano-1-methyl-3-(4,5-dicyano-1-methyl-2-imidazolyl)-2-imidazolone (10a).UV-Vis spectra of the newly synthesized compounds are described.

Synthesis and characterization of derivatives and dimers of 4,5- dicyanoimidazole

Synthesis of 1-methyl-2-fluoro-4,5-dicyanoimidazole was accomplished by halogen exchange between 1-methyl-2-bromo-4,5-dicyanoimidazole and potassium fluoride with catalytic 18-crown-6 ether in diglyme. Halogen exchange between 1-methyl-2-bromo-4,5-dicyanoimidazole and lithium chloride in N- methylpyrrolidinone at 150°C yielded 1-methyl-2-chloro-4,5-dicyanoimidazole, while additional heating to 210°C resulted in the subsequent demethylation to yield 2-chloro-4,5-dicyanoimidazole. The nucleophilic aromatic substitution reactions of various imidazole nucleophiles with 1-methyl-2- fluoro-4,5-dicyanoimidazole resulted in several derivatives of 2-(4',5'- dicyano-1'-imidanzoyl)-4,5-dicyanoimidazole. The pKa, UV, and electronic properties are reported.