Synthesis of 1-methyl-2-fluoro-4,5-dicyanoimidazole was done by haloge
n exchange between 1-methyl-2-bromo-4,5-dicyanoimidazole and potassium
fluoride. Halogen exchange between 1-methyl-2-bromo-4,5-dicyanoimidaz
ole and lithium chloride in N-methylpyrrolidinone at 150 degrees C yie
lded 1-methyl-2-chloro-4,5-dicyanoimidazole, and additional heating to
210 degrees C resulted in the demethylation to yield 2-chloro-4,5-dic
yanoimidazole. Thermolyses of the 2-halo-4,5-dicyanoimidazole derivati
ves (F, Cl) and 1-iodo-2-halo-4,5-dicyanoimidazole derivatives (Cl, Br
, I) between 100 and 290 degrees C were found to yield ,2-e]-1,3,5-tri
azine-2,3,5,6,8,9-hexacarbonitrile, or HTT, with (C5N4)(3) composition
. HTT has been characterized and purified and the crystal structure ob
tained. Thermolysis of HTT at 490-500 degrees C gives a material with
C/N = 1.020. The thermal properties of HTT and its decomposition produ
cts show thermal stability to 350 degrees C.