Tetrabromo-o-xylene

α,α,α',α'-Tetrabromo-o-xylene is an organobromine compound with the formula C₆H₄(CHBr₂)₂. Three isomers of α,α,α',α'-Tetrabromoxylene exist, but the ortho derivative is most widely studied. It is an off-white solid. The compound is prepared by the photochemical reaction of o-xylene with elemental bromine:

Reaction of α,α,α',α'-tetrabromo-o-xylene with sodium iodide affords α,α'-dibromo-o-xylylene, which can be trapped with dienophiles to give naphthylene. In the absence of trapping agents, the xylylene relaxes to α,α'-dibromobenzocyclobutane:

Cycloadditions of these xylylenes provides a pathway to acenes.

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