Synthesis and Characterization of 32 Polybrominated Diphenyl Ethers (original) (raw)

1999, Environmental Science & Technology

Polybrominated diphenyl ethers (PBDEs) are widely used as additive flame retardants in, for example, textiles, computers, television sets, and other electrical appliances. PBDEs are ubiquitous environmental contaminants, present also in humans. The environmental levels of the PBDEs are, however, still in general lower than those of polychlorinated biphenyls (PCBs). However, while the levels of PCBs generally are decreasing, those of the PBDEs are increasing in, for example, human milk. In the present study 32 individual PBDE congeners were synthesized and characterized. Physicochemical parameters including melting points and UV, 1 H NMR, and mass spectra are reported. Twenty-nine monobrominated to heptabrominated diphenyl ethers were synthesized by the coupling between four diphenyliodonium salts and nine phenolates. One tetrabromodiphenyl ether and two hexabromodiphenyl ethers were synthesized by bromination of two different PBDEs. Twenty-one of the PBDEs and two of the iodonium salts, 2,2′,4,4′-tetrabromodiphenyliodonium chloride and 3,3′,4,4′tetrabromodiphenyliodonium chloride, are to the authors' knowledge described for the first time. These synthesized reference compounds will aid in the identification and quantification of PBDEs present in environmental samples and will allow further assessment of PBDE toxicity.