The crystal structures of four bromoarenes based on 2,6-dimethylbromobenzene are reported, which are differentiated according the functional groupXplacedparato the Br atom:X= CN (4-bromo-3,5-dimethylbenzonitrile, C9H8BrN), (1),X= NO2(2-bromo-1,3-dimethyl-5-nitrobenzene, C8H8BrNO2), (2),X= NH2(4-bromo-3,5-dimethylaniline, C8H10BrN), (3) andX= OH (4-bromo-3,5-dimethylphenol, C8H9BrO), (4). The content of the asymmetric unit is different in each crystal,Z′ = ½ (X= CN),Z′ = 1 (X= NO2),Z′ = 2 (X= NH2), andZ′ = 4 (X= OH), and is related to the molecular symmetry and the propensity ofXto be involved in hydrogen bonding. In none of the studied compounds does the crystal structure feature other non-covalent interactions, such as π–π, C—H...π or C—Br...Br contacts.