Several ortho ‐carboranes bearing a phenoxy or a phenylamino group in the B9 position were prepared employing various protection and deprotection strategies. Following established protocols, dendritic compounds were synthesized from a hexachlorocyclotriphosphazene or thiophosphoryl chloride core, and possible anchoring options for the B9‐substituted ortho ‐carboranes were investigated experimentally and theoretically (DFT). Furthermore, 1‐ or 1,2‐phosphanyl‐substituted carborane derivatives were obtained. The resulting diethyl‐, diisopropyl‐, di‐ tert ‐butyl‐, diphenyl‐ or diethoxyphosphines bearing a tunable ortho ‐carborane moiety are intriguing ligands for future applications in homogeneous catalysis or the medicinal sector.