Tris 2,3-Dibromopropyl phosphate

Data were last reviewed in lARC (1979) and the eompound was elassified in lARC Monographs Supplement 7 (1987). 

126-72-7 Chem. Abstr. Name. 2,3-Dibromo-1-propanol phosphate (3 1) lUPAC Systematic Name-. 2,3-Dibromo-1-propanol phosphate Synonyms-. Phosphoric acid, tris(2,3-dibromopropyl) ester Tris 

2 Structural and molecular formulae and relative molecular mass 

Solubility-. Slightly soluble in water (0.8 mg/L at 24°C) miscible with carbon tetrachloride, chloroform and dichloromethane (Verschueren, 1996 United States National Library of Medicine, 1997) 

Production of tris(2,3-dibromopropyl) phosphate in the United States in 1975 was 

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FIBERS - REGENERATED CELLULOSICS] (Vol 10) (Tris(2,3-dibromopropyl)phosphate, TDBP) [126-72-7]... 

Mutagenic and later carciaogenic properties were found for tris(2,3-dibromopropyl) phosphate (148—150), a flame retardant used on polyester fabric ia the 1970s. This product is no longer on the market. The chemically somewhat-related tris(dichloroisopropyl) phosphate has been intensively studied and found not to display mutagenic activity (148,149,151). Tris(2-chloroethyl) phosphate appears to be a weak tumor-iaducer ia a susceptible rodent strain (150). 

Tris(2,2 -bipyridine)iron(3+) ion, 14 549 Tris(2,2 -bipyridine)iron(2+) ion, 14 549 Tris(2,2 -bipyridyl)ruthenium(II) complex chemiluminescence reagent, 5 856-857 Tris(2,3-dibromopropyl) phosphate, 11 502 Tris(2,3-dihydroxypropyl)isocyanurate, 8 204... 

Figure 2. Calibration curve for the glc-ecd analysis of tris (2,3-dibromopropyl)-phosphate on 3% SE-30 on Chromosorb W(HP) 100/120 mesh...

Figure 5. Thin-layer chromatogram of tris (2,3-dibromopropyl)phosphate on fluorescein impregnated silica gel solvent methylene chloride. Scan in fluorescence quench mom. (a) 3.7 /ig TRIS (b) 0.44 ttg TRIS.

Tris(2,3-dibromopropyl)phosphate (Tris), used to treat children s sleepwear to reduce flammability, was banned from use. The chemical was linked to kidney cancer in mice and rats and was mutagenic in bacteria. At the time it was used on 40-60% of children s sleepwear, mostly polyester, to enable it to meet federal requirements for flame retardance. 

Kluwe WM, McNish R, Smithson K, et al. 1981. Depletion by 1,2-dibromoethane, 1,2-dibromo-3-chloropropane, tris(2,3-dibromopropyl)phosphate, and hexachloro-1,3-butadiene of reduced non-protein sulfhydryl groups in target and non-target organs. Biochem Pharmacol 30 2265-2271. 

Dibromopropan-l-ol has been used as an intermediate in the preparation of flame retardants, insecticides and pharmaceuticals (Lewis, 1993). In particular, in the 1970s, the major use of 2,3-dibromopropan-l-ol was in the preparation of the flame retardant tris(2,3-dibromopropyl) phosphate, which was used in textiles production of this flame retardant other than for research purposes has been discontinued (WHO, 1995 lARC, 1999). 

Dibromopropan-l-ol has been detected in industrial discharges at levels of 0.5 mg/L (CEC, 1976) and is a hydrolysis product oftris(2,3-dibromopropyl) phosphate (St John et al., 1976). Tris(2,3-dibromopropyl) phosphate has been converted to 2,3-dibromopropan-l-ol by sewage sludge (Alvarez etal., 1982). 

Dibromopropan-l-ol, a metabolite of tris(2,3-dibromopropyl) phosphate, has been found in urine samples (at levels of up to 29 ng/mL) from 10 children who were wearing or who had worn tris(2,3-dibromopropyl) phosphate-treated nightwear (Blum etal., 1978). 

Dibromopropan-l-ol was used as an intermediate to produee the flame retardant tris(2,3-dibromopropyl) phosphate. In the past, it was deteeted in the urine of ehildren wearing nightwear treated with tris(2,3-dibromopropyl) phosphate. It is still produeed for use in the manufacture of other chemieals (possibly flame retardants, inseetieides and pharmaceuticals). 

Alvarez, G.H., Page, S.W. Ku, Y. (1982) Biodegradation of " C-tris(2,3-dibromopropyl)-phosphate in a laboratory activated sludge system. Bull, environ. Contam. Toxicol., 28, 85-90... 

Carr, H.S. Rosenkranz, H.S. (1978) Mntagenicity of derivatives of the flame retardant tris-(2,3-dibromopropyl) phosphate halogenated propanols. Mutat. Res., 57, 381-384... 

Holme, J.A., Soderlund, E.J., Hongslo, J.K,. Nelson, S.D. Dybing, E. (1983) Comparative genotoxicity studies of the flame retardant tris(2,3-dibromopropyl)phosphate and possible metabolites. Mutat. Res., 124, 213-224... 

Kerst, A.F. (1974) Toxicology of tris (2,3-dibromopropyl) phosphate. J. Fire Flammability/Fire Retard. Chem., Suppl. 1, 205-217... 

Lynn, R.K., Garvie-Gould, C., Wong, K. Kennish, J.M. (1982) Metabolism, distribution, and excretion of the flame retardant Tris(2,3-dibromopropyl) phosphate (Tris-BP) in the rat identification of mutagenic and nephrotoxic metabolites. Toxicol, appl. Pharmacol., 63, 105-119... 

Piival, M.J., McCoy, E.C., Gutter, B. Rosenkrantz, H.S. (1977) Tris(2,3-dibromopropyl) phosphate. Mutagenicity of a widely used flame retardant. Science, 195, 76-78... 

Simula, T.P, Glancey, M.J.. Soderlund. E.J., Dybing, E. Wolf, C.R. (1993) Increased mutagenicity of l,2-dibromo-3-chloropropane and tris (2,3-dibromopropyl) phosphate in Salmonella TAIOO expressing human glutathione S-transferases. Carcinogenesis, 14, 2303-2307... 

Tris(2,3-dibromopropyl) phosphate has been used as a flame retardant for plastics... 

Occupational exposures to tris(2,3-dibromopropyl) phosphate may have occurred during its production in the textile and polyurethane foam industries (lARC, 1979). 

Tris(2,3-dibromopropyl) phosphate was found in the air and soil in the United States in the 1970s. None was found in samples taken from various water and soil sources in Japan at this time. General population exposures may have occurred from the use of clothing treated with the compound (WHO, 1995). 

The American Conference of Governmental Industrial Hygienists (ACGIH) (1997) has not proposed any occupational exposure limit for tris(2,3-dibromopropyl) phosphate. Finland, Sweden and France have a carcinogen notation (United States National Library of Medicine, 1997). 

In a cohort mortality study in the United States, a group of 628 male workers was classified as exposed to tris(2,3-dibromopropyl) phosphate either on a routine or nonroutine basis 36 deaths occurred in this group (35 expected), seven of which were due to cancer compared with 6.6 that would have been expected (Wong et al., 1984). 

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