A simple methodology for the synthesis of heteroleptic diorganotelluride [2,6‐(Me2NCH2)2C6H3]TenBu (1) and homoleptic diorganotelluride [2,6‐(Me2NCH2)2C6H3]2Te (2) is reported. The halogenation reactions of diorganotelluride 1 are studied. In particular, the reaction of 1 with Br2 resulted in the isolation of a monoorgano dibromotelluronium(IV) cation, namely [2,6‐(Me2NCH2)2C6H3TeBr2]·Br3 ([3]·Br3). The reaction of [3]·Br3 with K2PdCl4 afforded a monoorgano mixed dihalotelluronium(IV) cation, [2,6‐(Me2NCH2)2C6H3TeClBr]·PdBr4 ([4]·PdBr4). When diorganotelluride 1 was treated with I2, the reaction afforded the tellurenium(II) cation, [2,6‐(Me2NCH2)2C6H3Te]·I2·I3 ([5]·I2·I3). The reaction of 1 with HgCl2 resulted in the isolation of dimeric diorganoditelluroxonium(IV) cation, [2,6‐(Me2NCH2)2C6H3Te(µ‐O)]2·Hg2Cl6 ([6]·Hg2Cl6). A similar diorganoditelluroxonium(IV) cation, namely [2,6‐(Me2NCH2)2C6H3Te(µ‐O)]2·2Br ([6]·2Br) was also obtained by the reaction of 1 with Br2 and NaOH. The crystallographic studies suggest that for each compound, both the N atoms from the pendant arms make strong Intramolecular Chalcogen Bonding (IChB) interactions with the Te center(s). The presence of a strong N→Te IChB interaction in the synthesized compounds was further validated by DFT calculations.