Polybrominated biphenyl (PBB) mixtures are contaminated with brominated naphthalenes formed during the synthesis procedure. Synthesis of hexabromonaphthalenes (HBNs) by direct bromination of naphthalene results in a mixture of two isomers. The identity of the major isomer, 1,2,3,4,6,7-HBN, was previously confirmed (Birnbaum et al., 1983). The minor isomer is definitively identified as 2,3,4,5,6,7-HBN by high-field nuclear magnetic resonance (NMR) spectroscopic analysis of brominated [1-13C]naphthalene-derived products. This isomer is extremely persistent and can be isolated from the liver of rats 10 d after treatment with the HBN mixture by a combination of solvent extraction and partition and adsorption chromatography.
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Birnbaum et al. (1985) studied this question.
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