10387. Hexabromocyclododecane
Nomenclature
Description and references
Brominated flame retardant; produced by bromination of 1,5,9-cyclododecatriene. Technical grade consists of a mixture of isomers, predominantly the α-, β-, and γ- enantiomeric pairs. Prepn of 2 crystalline forms: L. I. Zakharkin, V. V. Korneva, Dokl. Akad. Nauk. SSSR 132, 1078 (1960); G. Eglinton et al., J. Chem. Soc. C 1969, 474 DOI. Manufacturing processes: M. Minsinger et al., DE 1147574 (1963 to BASF); J. K. Kendall, US 6506952 (2003 to Albemarle Corp.). Absolute configuration of isomers: N. V. Heeb et al., Chemosphere 68, 940 (2007) DOI PubMed. Thermally-induced isomerization: R. Kppen et al., ibid. 71, 656 (2008) DOI PubMed. Biodegradation: J. W. Davis et al., Environ. Sci. Technol. 40, 5395 (2006) DOI PubMed. Enantiomer specific LC/MS/MS determn in food samples: B. Gómara et al., Anal. Chim. Acta 605, 53 (2007) DOI PubMed. Review of environmental fate: A. Covaci et al., Environ. Sci. Technol. 40, 3679-3688 (2006) DOI PubMed.
Properties
White powder or granules, mp 175-185°. Dec 220°. Vapor pressure: 6.3 × 105 Pa. Log P (octanol/water): 5.62. Insol in water. Sol in styrene, acetone.Derivative
α-HBCD.Nomenclature
Description and references
Pair of enantiomers having the relative configuration (1R,2R,5S,6R,9R,10S).
Properties
Soly in water: 48.8 μg/l. d 2.338.Derivative
β-HBCD.Nomenclature
Description and references
Pair of enantiomers having the relative configuration (1R,2S,5R,6R,9R,10S).
Properties
Soly in water: 14.7 μg/l. d 2.412.Derivative
γ-HBCD.Nomenclature
Description and references
Pair of enantiomers having the relative configuration (1R,2R,5R,6S,9S,10R). Predominant form in technical grade product; isomerizes to α-form at temperatures above 160°.