| Compound Name |
Pentabromodiphenyl ether |
| Stockholm Annex code | I, IV |
| Key |
Annex I to the regulation are subject to prohibition (with specific exemptions) on manufacturing, placing on the market and use; Annex II to the regulation are subject to restriction on manufacturing, placing on the market and use; Annex III to the regulation are subject to release reduction provisions; and Annex IV to the regulation are subject to waste management provisions. Note that for some substances listed in Annex I, specific exemptions on the prohibition of their use, manufacturing and placing on the market may apply. |
| Classification |
Intentional production |
| Category |
Listed under Annex A with a specific exemption for use as articles containing these chemicals for re |
| Year of Listing Decision |
2009 |
| Persistence |
N/A |
| Specific exemptions associated with its use |
Production: None |
| Acceptable purposes associated with its use |
Use: Articles in accordance with the provisions of Part V of Annex A It is sometimes used as a flame retardant in flexible polyurethane foam. Used in the manufacture of printed circuit boards |
| Conventions on POPs |
Stockholm Convention Convention on Long-Range Transboundary Air Pollution Rotterdam Convention Basel Convention |
| Name |
Pentabromodiphenyl ether |
| Synonyms |
2,2',4,4',5-Pentabromodiphenyl ether 1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene Benzene,1,2,4-tribromo-5-(2,4-dibromophenoxy)- Benzene, 1,1'-oxybis-, pentabromo deriv. BDE-99 2,2',4,4',5-PentaBDE 2,2',4,4',5-Pentabromodiphenyl ether solution 2,4-Dibromophenyl 2,4,5-tribromophenyl ether Oxyde de diphenyle, derive pentabrome Difenil eter, derivado pentabromado penta-BDE Pentabromodiphenyl oxide |
| Structure | Br)OC2=CC(=C(C=C2Br)Br)Br.png)
Molecular Formula:
C12H5Br5O
|
| CAS Number | 32534-81-9 |
| European Community (EC) Number | 251-084-2 |
| European Chemicals Agency (ECHA) | 251-084-2 |
| PubChem ID | 36159 |
| DSSTOX Substance ID | DTXSID2024246 |
| KEGG | C18203 |
| ChemSpider |
33255 |
| Similarity threshold | Name of Related Compound | DSSTox Substance ID | CAS Number | Molecular weight | Molecular formula |
|---|---|---|---|---|---|
| Markush Child | 2,2',4,4',5-Pentabromodiphenyl ether | DTXSID9030048 | 60348-60-9 | 564 g/mol | C12H5Br5O |
| Markush Child | 2,2',3,4,4'-Pentabromodiphenyl ether | DTXSID4052685 | 182346-21-0 | 564 g/mol | C12H5Br5O |
| Markush Child | 2,2',4,4',6-Pentabromodiphenyl ether | DTXSID4052689 | 189084-64-8 | 564 g/mol | C12H5Br5O |
| Markush Child | Benzene, 1,2,3-tribromo-4-(2,3-dibromophenoxy)- | DTXSID20477018 | 327185-11-5 | 564 g/mol | C12H5Br5O |
| Markush Child | 1,2,3,4,5-Pentabromo-6-phenoxybenzene | DTXSID80548894 | 189084-65-9 | 564 g/mol | C12H5Br5O |
| Markush Child | 1,2,3-Tribromo-5-(3,4-dibromophenoxy)benzene | DTXSID50573491 | 366791-32-4 | 564 g/mol | C12H5Br5O |
| Markush Child | 1,2,4-Tribromo-5-(3,4-dibromophenoxy)benzene | DTXSID40724016 | 446254-80-4 | 564 g/mol | C12H5Br5O |
| Markush Child | 1,2,4,5-Tetrabromo-3-(2-bromophenoxy)benzene | DTXSID90785354 | 446254-60-0 | 564 g/mol | C12H5Br5O |
| Markush Child | 1,2,4-Tribromo-5-(3,5-dibromophenoxy)benzene | DTXSID30785570 | 417727-71-0 | 564 g/mol | C12H5Br5O |
| Markush Child | 1,3,5-Tribromo-2-(2,3-dibromophenoxy)benzene | DTXSID10855048 | 38463-82-0 | 564 g/mol | C12H5Br5O |
| N/A | Full List of Related compounds | N/A | N/A | N/A g/mol | N/A |
| Description | Reference | Article Link |
|---|---|---|
| Polybrominated diphenyl ethers (PBDEs) are found in fire retardants used in plastic cases of televisions and computers, electronics, carpets, lighting, bedding, clothing, car components, foam cushions, and other textiles. The commercial PBDE products predominantly consist of so-called penta-, octa-, and decabromodiphenyl ether products. Today, decabromodiphenyl ether (deca-BDE) is the largest product on the market and makes up over 80% of the total production of PBDEs, whereas pentabromodiphenyl ether (penta-BDE) and octabromodiphenyl ether (octa-BDE) products constitute approximately 12% and 6%, respectively, of the total PBDEs production. PBDEs have recently been found in indoor and outdoor air, and dust samples. Furthermore, several regional studies have shown increasing concentrations in human milk, tissue, and serum samples, with the most prevalent PBDE congeners in human samples being PBDE-47 and PBDE-99. Therefore, the widespread uses of PBDEs and increased amount of contamination in the environment have led to rising concern about the possible adverse health effects in humans. | Kim and Lee., 2011. Endocrine Disrupting Chemicals and Human Cancer | Link |
| Polybrominated diphenyl ethers (PBDEs) are a class of synthetic chemicals first produced commercially in the 1970s. They are added to products such as foam padding, textiles, or plastics to retard combustion. 2,2?,4,4?,5,5?-hexabromobiphenyl (BB-153) is a brominated biphenyl that was used as a flame retardant in the U.S. until the 1970s. Its use was phased out following an accidental contamination of cattle feed in the state of Michigan with the contamination extending to other animals, the environment, and into humans. Three major commercial mixtures of PBDEs have been produced and used. These are named for the average number of bromines attached to the diphenyl ether structure, e.g., pentaBDE. The pentaBDE technical mixture contains 50-60% of PBDE congeners with five bromines, 24-38% with four bromines (tetraBDEs) and 4-8% with six bromines (hexaBDE), though reports on mixtures vary. Commercial pentaBDEs are often added to polyurethane foams used in mattresses, upholstered furniture, and carpet padding. OctaBDE technical mixtures contain 10-12% of PBDE congeners with six bromines, 43-44% with seven bromines, 31 35% with eight bromines and 10-11% with nine bromines. OctaBDE mixtures are added to acrylonitrile-butadiene-styrene used in computer and appliance casings, and also to some polyolefins and nylon. DecaBDE is the most widely used PBDE globally and greater than 97% of its content includes PBDEs with ten bromines. It is added to polystyrene, polybutylene, nylon, polypropylene, and other thermoelastic polymers used in adhesives, wire insulation, casings for televisions and computers, and in some non-clothing textiles. PBDEs are often combined with antimony trioxide to enhance the fire protection offered by the PBDEs. For example, protected polypropylene can contain 23% decaBDE and 8% antimony trioxide by weight. PBDE content in protected products varies from 3-33%. PBDE production makes up about 25% of all fire retardant production. In 2000, global production was 67,000 metric tons annually with about 80% of the total being decaBDE. Most of the pentaBDE produced has been used within the U.S. About 40% and 44% of the global production of octaBDE and decaBDE were also used in the U.S.Since PBDEs are not chemically bound to the flame-retarded material, they can enter the environment from volatilization, leaching, or degradation of PBDE-containing products. Also, PBDEs can enter the environment from manufacturer-related releases. When thermally decomposed, PBDEs can produce polybrominated dibenzo-p-dioxins and dibenzofurans. Manufacturers of pentaBDE and octaBDE in the U.S. were to have phased out production of these chemicals by 2004 and U.S. EPA issued a rule to prevent new production. PBDEs are generally persistent in the environment and have been measured in aquatic sediments and aquatic and terrestrial animals, especially in fish where PBDEs are known to bioconcentrate. Several studies of stored biologic specimens have shown dramatic increases in PBDE concentrations over the last several decades, for example, in archived bird eggs. Human exposure to PBDEs is thought to result from dietary sources, including fish, fatty foods, and mother’s milk. However, oral ingestion from dust and leachates may be a larger source, particularly for children. Once absorbed, PBDEs distribute into body fat. The metabolism and elimination of PBDEs in humans are not well characterized. One occupational study indicated that decaBDE has an elimination half-life of 11-18 days and the octaBDEs have half-lives ranging between 37-91 days. In animals, PBDE elimination occurs primarily through fecal excretion with decaBDE being more rapidly eliminated than the other less brominated PBDEs. Some PBDEs measured in human serum by the National Biomonitoring Program. | CDC Biomonitoring Program accessed 09 October 2020 | Link |
| Polybrominated diphenyl ethers (PBDEs) are industrial chemicals whose concentrations are rising exponentially in the aquatic environment. They are similar to PCBs, with a basic diphenyl ether structure substituted with up to 209 possible combinations of bromine atoms on both rings. The sources of these persistent chemicals are diffuse, with a major source thought to be PBDE flame retardants leaching from everyday products such as textiles, computers, furniture foam, plastics, electronics, automobiles, and construction materials. The polymeric materials in these products can contain 5–25% PBDE by weight. Despite very recent reduction in the manufacture of PBDEs, plastic products containing these flame retardants will continue to leach PBDEs into the environment for years to come. | Echols et al., 2009. Pollution of Aquatic Ecosystems II: Hydrocarbons, Synthetic Organics, Radionuclides, Heavy Metals, Acids, and Thermal Pollution. | Link |