Five 2-aminochalcone derivatives [R = H(1), R = OCH2CH3(2), R = 2,4,5-OCH3(3), R = 3,4,5-OCH3(4), and R = thiophene(5)] were synthesized and characterized by H-1 NMR, FT-IR, and UV-Vis spectroscopy. Crystal structure of 2 was also determined by single crystal X-ray diffraction. Compound 2 crystallizes in a monoclinic P2(1)/n space group with the unit cell parameters a = 32.804(7) angstrom, b = 4.9972(11) angstrom, c = 21.7173(3) angstrom, beta = 128.440(4)degrees, V = 2788.4(10) angstrom(3), and Z = 8. There are two molecules in an asymmetric unit of 2, the molecular structure of 2 is twisted with the dihedral angle between the two phenyl rings being 13.6(3)degrees in one molecule and 7.1(3)degrees in the other. In the crystal packing, the molecules of 2 are linked into chains along the b-axis by C-H center dot center dot center dot O interactions. Antioxidant and antibacterial activities of 1-5 were also carried out.