1,2,4,5-Tetrabromobenzene
chemical compound
1,2,4,5-Tetrabromobenzene is an aryl bromide and a four-substituted bromobenzene with the formula C6H2Br4. It is one of three isomers of tetrabromobenzene. The compound is a white solid. 1,2,4,5-Tetrabromobenzene is an important metabolite of the flame retardant hexabromobenzene.
Preparation
The synthesis of 1,2,4,5-tetrabromobenzene has already been reported in 1865 from benzene and excess bromine in a sealed tube at 150 °C. However, the clearly reduced melting point of about 160 °C indicates impurities in the final product. In his 1885 dissertation, Adolf Scheufelen published the synthesis of a purer sample using iron(III) chloride FeCl3 as a catalyst, isolated as "pretty needles" ("schönen Nadeln").
The synthesis can also be carried out in solution in chloroform or tetrachloromethane and yields 1,2,4,5-tetrabromobenzene in 89% yield. This reaction can also be carried out in a laboratory experiment with excess bromine and iron nails (as starting material for iron (III) bromide FeBr3). The intermediate stage is 1,4-dibromobenzene, which reacts further with excess bromine to give 1,2,4,5-tetrabromobenzene.
Reactions
Building block for liquid crystals and fluorescent dyes
Owing to its symmetrical structure and reactivity, 1,2,4,5-tetrabromobenzene is a precursor to nematic liquid crystals with crossed mesogens and for columnar (discotic) liquid crystals with an extensive planar, "board-like" tetrabenzoanthracene core.
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