A new azo-bridged pyridine derivative (E)-1, 2-bis(2-chloro-3-nitropyridin-4-yl) diazene (3) and 2-chloro-4-amine-3, 5-dinitropyridine (2) were synthesized through a direct nitration reaction using 2-chloro-4-aminopyridine(1) as a primary material, followed by a simple amination reaction to give (E)-1, 2-bis(2-amino-3-nitro-pyridin-4-yl)diazene(5) and 2, 4-diamino-3, 5-dinitropyridine(4), with a total yield of 69% and 18%, respectively. Red colored crystals of compound 3 growing from CHCl₃ solvent at room temperature were used for X-ray diffraction analysis. The detonation performances of compounds 4 and 5 were calculated by Kamlet-Jacobs empirical equations. The results show that the crystal of compound 3 is monoclinic, space group P2₁/N with crystal parameters of a=9.965(2) Å, b=6.3190(13) Å, c=10.737(2) Å, β= 93.75(3)°, V=674.6(2) ų, D_c=1.689 g·cm^-3, C₁₀H₄Cl₂N₆O₄, M_r=171.55, F(000)=344, μ(Mo K_α)=0.510 mm^-1, and Z=4. The detonation performance of compound 4 is similar to 2, 4, 6-trinitrotoluene (TNT), whereas the detonation performance of compound 5 is poor.