Bis bromomethyl propane-l,3-diol

Name 2,2-Bis(bromomethyl)propane-l,3-diol 

2 Structural and molecular formulae and relative molecular mass 

2-Bis(bromomethyl)propane-l,3-diol is currently available with a purity of 98.5% (Ameribrom, 1996 Dead Sea Bromine Group, 1998). 2,2- Bis(bromomethyl)-propane-l,3-diol was available earlier as a technical product with a purity of 79%. Several impurities were identified in the technical product 2,2-bis(hydroxymethyl)-l-bromo-3-hydrox ropane, 2,2-bis(bromomethyl)-l-bromo-3-hydroxypropane and pentaerythritol (National Toxicology Program, 1996). 

Trade names for 2,2-bis(bromomethyl)propane-l,3-diol include FR-522 and FR-1138. 

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Chem. Abstr. Name 2,2-Bis(bromomethyl)propane-l,3-diol... 

Bis(bromomethyl)propane-l,3-diol is a reactive flame retardant that is used primarily in unsaturated polyester resins for moulded products and in rigid polyurethane... 

Bis(bromomethyl)propane-l,3-diol may enter the enviromnent as fugitive dust, through wastewater and through disposal of resins and foams which may contain the compoimd as an impurity. 2,2-Bis(bromomethyl)propane-l,3-diol may be persistent in water (Environmental Protection Agency, 1983 Elwell et al., 1989 Durmick et al., 1997). No data were available to the Working Group on levels of 2,2-bis(bromo-methyl)propane-l,3-diol in the environment. 

Groups of 60 male and 60 female B6C3Fi mice, six weeks of age, were fed diets containing 0,312,625 or 1250 mg/kg diet (ppm) 2,2-bis(bromomethyl)propane-l,3-diol (technical grade FR-1138 with a composition of 78.6% 2,2-bis(bromomethyl)-... 

Table 1. Neoplastic lesions in mice treated with 2,2-bis(bromomethyl)-propane-l,3-diol in the diet...

Thirteen-week toxicity studies of 2,2-bis(bromomethyl)propane-l,3-diol were conducted in male and female Fischer 344/N rats and B6C3Fi mice to determine target organ toxicity. 2,2-Bis(bromomethyl)propane-l,3-diol (technical grade, 78.6% pure) was administered by gavage in com oil for five days per week to rats, 6-7 weeks of age, at doses of 0, 50, 100, 200, 400 or 800 mg/kg bw and to mice, 6-9 weeks of age. 

Bis(bromomethyl)propane-l,3-diol eaused a dose-related inerease in chromosomal aberrations in Chinese hamster ovary cells, but only at doses that eaused significant cytotoxicity a majority of the breaks were located in the heteroehromatie region of the long arm of ehromosome X, but the reasons for this are unclear. Induetion of sister chromatid exchanges in Chinese hamster ovary cells was judged to be equivoeal. 

Bis(bromomethyl)propane-l,3-diol caused significant increases in miero-nucleated normoehromatie erythroeytes in peripheral blood samples from male and female mice exposed for 13 weeks via the diet, whereas in tests for mieronueleus formation in mouse bone marrow, results were positive for females but ineonsistent for males [routes of administration were different]. 

Bis(bromomethyl)propane-l,3-diol is a flame retardant used in polyester resins and polyurethane foams. No data on human exposure to this substance were available. 

No effects were observed, after 13 weeks exposure, on sperm parameters or vaginal cytology in mice or rats. However, in a mouse continuous breeding study, exposure to 2,2-bis(bromomethyl)propane-l,3-diol in feed caused a female-specific decrease in reproductive capacity. 

Bis(bromomethyl)propane-l,3-diol was mutagenic in only one of several bacterial strains tested, and only with metabolic activation. In cultured mammalian cells, it was only weakly active in tests for chromosomal aberrations and sister chromatid exchanges. Micronucleus formation, indicative of chromosomal damage, was induced in cells from mice exposed to 2,2-bis(bromomethyl)propane-l,3-diol in vivo. 

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