New heterobifunctional oligomeric energetic plasticizer with alkyne at one end and a hydroxyl group at the other end, was synthesized via ring opening polymerization of glycidyl nitrate monomer, propargyl alcohol as initiator and BF3 as a catalyst. The terminal hydroxyl group of plasticizer capped with methoxy and acetyl groups to generate two other types of reactive plasticizer. The chemical structure of plasticizers has characterized by FT-IR and H-1 NMR spectroscopy as well as DSC, and TGA methods. Also, plasticizers reactivity toward alkyne-azide reaction, have evaluated through LUMO energy level calculation of reactive plasticizer that containing one and two repeating units in their structure. Moreover, the results show that grafting up to 10% of the total amount of azide groups of GAP, reduces the viscosity and the glass transition temperature of GAP-g-PGN copolymer in comparison to glycidyl azide polymer.