It is an off-white solid that, like other benzyl halides, is strongly lachrymatory.
It is a useful reagent owing to the convenient reactivity of the two C-Br bonds.
It is prepared by the photochemical reaction of ortho-xylene with bromine:[2] Further bromination gives the tetrabromide:[3] Upon reaction with thiourea followed by hydrolysis of the intermediate bisisothiouronium salts, xylylene dibromide can be converted to the dithiol C6H4(CH2SH)2.
This species can be trapped when the dehalogenation is conducted in the presence of iron carbonyl.
[5] Coupling of xylylene dibromide by treatment with lithium metal gives dibenzocyclooctane, precursor to dibenzocyclooctatetraene.