In this work, the vibrational spectral analysis was carried out using Raman and Infrared spectroscopy (solid phase) in the range 4000-400cm-1 and 3500 cm-1, respectively, for the 2-Chloro-5-Trifluoromethyl pyridine (2C5TFMP).Simulation of Infrared and Raman spectra utilizing the results of these calculations led to good agreement with the observed spectral patterns. The complete assignments were performed on the basis of the potential energy distribution (PED) of the vibrational modes, calculated with scaled quantum mechanics (SQM) method. The molecular structure and fundamental vibrational frequencies have been obtained from density functional theory (DFT) B3LYP methods with 6-311++G (d, p) basis set calculations. The investigation in view of NMR chemical shift, First Order Hyperpolarizability, Molecular Electrostatic Potential Map (MESP) and Thermo dynamical functions have been carried out. The observed HOMO LUMO mappings reveal the charge transfer possibilities within the molecule. Natural Bond Orbital analysis, Mulliken charges, electrostatic potential charges are also computed.