A series of azo functionalized diols were synthesized through diazotization which involves the reaction of amine with phenol and 2,6-dimethyl phenol. Four different amines have been used to prepare five bisphenols. These bisphenols were converted to their corresponding cyanate esters by treatment with cyanogen bromide (BrCN) in the presence of triethylamine (Et3N). The chemical structures of the prepared compounds were characterized with Fourier Transform Infrared, H-1-NMR, C-13-NMR spectroscopy, and elemental analysis. Dynamic curing behavior was investigated using differential scanning calorimetry. The maximum curing temperature of these cyanate esters are in the range of (186-208 degrees C). T-g values of the polycyanurate networks are in the range of 245-276 degrees C. The thermal properties of cured cyanate ester were studied at a heating rate of 10 degrees C min(-1) in N-2 atmosphere. The polymers showed excellent thermal stability (T-10 was found to be in the range 405-438 degrees C) and the percentage of char yield at 800 degrees C were found to be 30-49. The flame retardancy of the cyanate ester resins have been studied using limited oxygen index value which is in the range of 29.5-37.1 at 800 degrees C. POLYM. ENG. SCI., 55:47-53, 2015. (c) 2014 Society of Plastics Engineers