10400. Tetrabromobisphenol A

Nomenclature

CAS number: 79-94-7
4,4′-(1-Methylethylidene)bis[2,6-dibromophenol]; 4,4′-(1-isopropylidene)bis[2,6-dibromophenol]; 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane; TBBA; TBBPA; BA-59P (Chemtura); Fire Guard 2000 (Teijin); Saytex CP-2000 (Albemarle).
C15H12Br4O2; mol wt 543.87.
C 33.13%, H 2.22%, Br 58.77%, O 5.88%.

Description and references

Brominated flame retardant used in the formulation of thermoplastic resins for electronics. Prepn: T. Zincke, M. Grüters, Ann. 343, 75 (1905). Manufacturing process: A. J. Dietzler, US 3029291 (1962 to Dow); H. E. Hennis, Ind. Eng. Chem. Prod. Res. Dev. 2, 140 (1963) DOI. Fire retardant properties: J. A. Schneider et al., ibid. 9, 559 (1970) DOI. Crystal structure: J. Eriksson, L. Eriksson, Acta Crystallogr. C57, 1308 (2001) DOI PubMed. Polymerization reaction kinetics: F. Barontini et al., Ind. Eng. Chem. Res. 39, 855 (2000) DOI. Thermal degradation: idem et al., ibid. 43, 1952 (2004) DOI. Photodegradation: J. Eriksson et al., Chemosphere 54, 117 (2004) DOI. Toxicokinetics: U. M. D. Schauer et al., Toxicol. Sci. 91, 49 (2006) DOI PubMed. Review of toxicology: Tetrabromobisphenol A (National Toxicology Program, USDHHS, 2002) 33pp. Review of environmental analysis methods: A. Covaci et al., J. Chromatogr. A 1216, 346-363 (2009) DOI PubMed.

Chemical structure

Properties

Crystals from isopropyl alcohol, mp 181-182°. bp ≈316°. pKa1 7.5; pKa2 8.5. uv max (water): 310 nm (ε 9170). Crystal density: 2.158. Log P (octanol/water): 4.5. Soly in water (mg/l): 0.72 (15°); 4.16 (25°); 1.77 (35°). Sol in methanol, ether, chloroform, acetone, benzene, methylene chloride, methyl ethyl ketone. LD50 in rats, mice (mg/kg): >2000, >2000 orally; ≥3200, ≥3200 i.p. (USDHHS).

Use

Reactive flame retardant in epoxy and polycarbonate resins; additive flame retardant in acrylonitrile-butadiene-styrene (ABS) resins.