A series of derivatives of (E)-6-chloro-5-fluoro-2-styryl-1H-benzo[d]imidazole, and 5-fluoro-2-methylN-phenyl-1H-benzo[d]imidazol-6-amine was synthesized. Compounds confirmed by melting point, FT-IR, 1HNMR, Mass spectral analytical techniques and predicted for their ADME, Pharmacokinetic properties.Synthesized compounds screened for better antibacterial and antiinflammatory activity. To synthesize a series of novel trisubstituted fluorinated benzimidazole derivatives and evaluate the physicochemical, ADME and pharmacokinetic properties and biological activity. The starting material Flouro-chloro-aniline ona series of reaction such as acetylation, nitration, deacetylation followed by reductionto get 4-fluoro-5-chloroorthophenylene diamine. The di-amino compound cyclized with acetyl chloride to obtain 6-chloro-5-fluoro-2- methyl-1H-benzimidazole which on reaction with various aromatic aldehyde forms series of compounds 31(a-h), and with various anilines forms compounds 32(a-j). Physicochemical, ADME and pharmacokinetic properties predicted Insilco. Antimicrobial activity screened by Agar diffusion method. In vitro antiinflammatory activity screened by protein denaturation assay.The compounds synthesized confirmed by melting Point, FT-IR, 1HNMR, Mass spectral analytical techniques and predicted for their ADME, Pharmacokinetic properties in silico. The compounds screened and confirmed with moderate antimicrobial, and in vitro antiinflammatory activity.