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{{chembox
{{chembox <!--Chembox data refers to congener BDE-99. See text for further details-->
| Verifiedfields = changed
| ImageFile = Pentabromodiphenyl ether BDE-99.svg
| Watchedfields = changed
| ImageSize =
| verifiedrevid = 405763611
| ImageFile2 = Pentabromodiphenyl ether3d.png
| ImageFile = Polybrominated diphenyl ether.svg
| ImageSize2 = 220px
| ImageSize = 200px
| IUPACName = 1,2,4-tribromo-5-(2,4-dibromophenoxy)<br>benzene
| ImageCaption = General chemical structure of pentabromodiphenyl ethers, where ''n'' + ''m'' = 5
| OtherNames = PentaBDE, Penta-BDE, PeBDE, penta, PBDPO
| IUPACName =
| Section1 = {{Chembox Identifiers
| OtherNames = PentaBDE; Penta-BDE; PeBDE; Penta; PBDPO; Pentabromobiphenyl ether
| Abbreviations =
|Section1={{Chembox Identifiers
| CASNo = 32534-81-9
| EINECS = | Abbreviations =
| index1_label = 2,2',4,4',5
| PubChem = 36159
| index2_label = 2,2′,4,4′,6
| SMILES =
| CASNo_Ref = {{cascite|correct|CAS}}
| InChI =
| CASNo = 32534-81-9
| RTECS =
| CASNo1_Ref = {{cascite|correct|CAS}}
| MeSHName =
| CASNo1 = 60348-60-9
| ChEBI =
| CASNo2_Ref = {{cascite|correct|CAS}}
| KEGG =
| CASNo2 = 189084-64-8
| ATCCode_prefix =
| EINECS = 251-084-2
| ATCCode_suffix =
| PubChem1 = 36159
| ATC_Supplemental =}}
| PubChem2 = 154083
| Section2 = {{Chembox Properties
| ChemSpiderID_Ref =
| Formula = C<sub>12</sub>H<sub>5</sub>Br<sub>5</sub>O
| ChemSpiderID1 = 33255
| MolarMass = 564.69 g/mol
| MeSHName =
| Appearance = amber solid or coarse white powder
| Density = | KEGG1 = C18203
| UNII_Ref = {{fdacite|correct|FDA}}
| MeltingPt = | Melting_notes =
| UNII = 7REL09ZX35
| BoilingPt = | Boiling_notes =
| UNII1_Ref = {{fdacite|correct|FDA}}
| Solubility = not soluble
| UNII1 = D3A2T91I1E
| SolubleOther =
| UNII2_Ref = {{fdacite|correct|FDA}}
| Solvent =
| pKa = | UNII2 = YW2W2K0A6U
| pKb = }} | KEGG_Ref =
| RTECS = DD6625350
| Section3 = {{Chembox Structure
| UNNumber = 3152 3077
| CrystalStruct =
| Coordination = | ChEBI1 = 81582
| MolShape = }} | ChEBI2 = 138065
| ChEMBL1 = 374400
| Section4 = {{Chembox Thermochemistry
| InChI1=1S/C12H5Br5O/c13-6-1-2-11(9(16)3-6)18-12-5-8(15)7(14)4-10(12)17/h1-5H
| DeltaHf =
| InChIKey1 = WHPVYXDFIXRKLN-UHFFFAOYSA-N
| DeltaHc =
| SMILES1 = C1=CC(=C(C=C1Br)Br)OC2=CC(=C(C=C2Br)Br)Br
| Entropy =
| InChI2=1S/C12H5Br5O/c13-6-1-2-11(8(15)3-6)18-12-9(16)4-7(14)5-10(12)17/h1-5H
| HeatCapacity = }}
| InChIKey2 = NSKIRYMHNFTRLR-UHFFFAOYSA-N
| Section6 = {{Chembox Explosive
| SMILES2 = C1=CC(=C(C=C1Br)Br)OC2=C(C=C(C=C2Br)Br)Br
| ShockSens =
}}
| FrictionSens =
|Section2={{Chembox Properties
| ExplosiveV =
| REFactor = }} | C=12 | H=5 | Br=5 | O=1
| Appearance = Viscous white to amber-colored liquid<ref name=GESTIS>{{GESTIS|ZVG=24350}}</ref>
| Section7 = {{Chembox Hazards
| Density = 2.25-2.28 g/cm<sup>3</sup><ref name=GESTIS/>
| ExternalMSDS =
| EUClass = | MeltingPtC = -7 to 3
| EUIndex = | MeltingPt_ref=
| BoilingPt = Decomposes
| MainHazards =
| BoilingPt_ref= <ref name=GESTIS/>
| NFPA-H =
| Solubility = not soluble
| NFPA-F =
| NFPA-R = | SolubleOther =
| Solvent =
| NFPA-O =
| pKa =
| RPhrases = {{Rlink|R48/21/22}}, {{Rlink|R50/53}}, {{R64}} <!-- from http://www.hvbg.de/d/bia/gestis/stoffdb -->
| pKb = }}
| SPhrases = {{(S1/2)}}, {{S36/37}}, {{S45}}, {{S60}}, {{S61}} <!-- from http://www.hvbg.de/d/bia/gestis/stoffdb -->
|Section3={{Chembox Structure
| RSPhrases =
| FlashPt = | CrystalStruct =
| Autoignition = | Coordination =
| ExploLimits = | MolShape = }}
|Section4={{Chembox Thermochemistry
| PEL = }}
| DeltaHf =
| Section8 = {{Chembox Related
| OtherAnions = | DeltaHc =
| OtherCations = | Entropy =
| HeatCapacity = }}
| OtherFunctn = ], ]
|Section7={{Chembox Hazards
| Function = ]s
| LD50 = 5000 mg/kg (oral, rat)<ref name=GESTIS/>
| OtherCpds = ] }}
| ExternalSDS =
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| NFPA-S =
| GHSPictograms = {{GHS08}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|362|373|410}}
| PPhrases = {{P-phrases|}}
| FlashPt =
| AutoignitionPt =
| ExploLimits =
| PEL = }}
|Section8={{Chembox Related
| OtherAnions =
| OtherCations =
| OtherFunction = ], ]
| OtherFunction_label = ]s
| OtherCompounds = ] }}
}} }}
'''Pentabromodiphenyl ether''' (also known as '''pentabromodiphenyl oxide''') is a ] which belongs to the group of ] (PBDEs). Because of their toxicity and persistence, their industrial production is to be eliminated under the ], a treaty to control and phase out major ] (POP). '''Pentabromodiphenyl ether''' (also known as '''pentabromodiphenyl oxide''') is a ] which belongs to the group of ] (PBDEs). Because of their toxicity and persistence, their industrial production is to be eliminated under the ], a treaty to control and phase out major ] (POP).


==Composition, uses, and production== ==Composition, uses, and production==
'''Commercial pentaBDE''' is a technical mixture of different PBDE ]s, with BDE-47 (2,2',4,4'- tetrabromodiphenyl ether) and BDE-99 (2,2',4,4',5-pentabromodiphenyl ether, pictured in the Infobox) as the most abundant.<ref name=UNEP2007>Ad hoc working group on pentabromodiphenyl ether under the Persistent Organic Pollutants Review Committee of the Stockholm Convention. United Nations Environment Programme, August 2007.</ref> The term '''pentaBDE''' alone refers to ]s of pentabromodiphenyl ether (PBDE congener numbers 82-127).<ref name=ATSDR2004>Agency for Toxic Substances and Disease Registry. Atlanta, GA: U.S. Department of Health and Human Services, Public Health Service, September 2004.</ref> Commercial pentaBDE is a technical mixture of different PBDE ]s, with BDE-47 (2,2',4,4'- tetrabromodiphenyl ether) and BDE-99 (2,2',4,4',5-pentabromodiphenyl ether) as the most abundant.<ref name=UNEP2007>Persistent Organic Pollutants Review Committee of the Stockholm Convention. United Nations Environment Programme, August 2007.</ref> The term '''pentaBDE''' alone refers to ]s of pentabromodiphenyl ether (PBDE congener numbers 82-127).<ref name=ATSDR2004>Agency for Toxic Substances and Disease Registry. {{Webarchive|url=https://web.archive.org/web/20071031065336/http://www.atsdr.cdc.gov/toxprofiles/tp68.html |date=2007-10-31 }} Atlanta, GA: U.S. Department of Health and Human Services, Public Health Service, September 2004.</ref>


{| class="wikitable" {| class="wikitable"
|+ Composition of commercial pentaBDE <ref>M. J. La Guardia, R. C. Hale, E. Harvey: ''Detailed Polybrominated Diphenyl Ether (PBDE) Congener Composition of the Widely Used Penta-, Octa-, and Deca-PBDE Technical Flame-retardant Mixtures'', ], 2006, 40, 6247–6254, {{DOI|10.1021/es060630m}}.</ref> |+ Composition of commercial pentaBDE <ref>M. J. La Guardia, R. C. Hale, E. Harvey: ''Detailed Polybrominated Diphenyl Ether (PBDE) Congener Composition of the Widely Used Penta-, Octa-, and Deca-PBDE Technical Flame-retardant Mixtures'', ], 2006, 40, 6247–6254, {{doi|10.1021/es060630m}}.</ref>
! Structure ! Structure
! Congener ! Congener
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| BDE-47 | BDE-47
| 2,2′,4,4′-tetra-<br />bromodiphenyl ether | 2,2′,4,4′-tetra-<br />bromodiphenyl ether
| 38–42 % | 38–42%
|- |-
| ] | ]
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| BDE-99 | BDE-99
| 2,2′,4,4′,5-penta-<br />bromodiphenyl ether | 2,2′,4,4′,5-penta-<br />bromodiphenyl ether
| 45–49 % | 45–49%
|- |-
| ] | ]
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| 2.7–4.5 % | 2.7–4.5 %
|} |}
<small>Only congeners with more than 1 % listed.</small> <small>Only congeners with more than 1% listed.</small>


Commercial pentaBDE is most commonly used as a flame retardant in flexible ] foam; it was also used in ]s in Asia, and in other applications.<ref name=UNEP2007/> The annual demand worldwide was estimated as 7,500 ]s in 2001, of which the Americas accounted for 7,100 tonnes, Europe 150 tonnes, and Asia 150 tonnes.<ref>Bromine Science and Environmental Forum. {{webarchive|url=https://web.archive.org/web/20061130221642/http://www.bsef.com/docs/BFR_vols_2001.doc |date=2006-11-30 }} 21 January 2003.</ref> The global industrial demand increased from 4,000 tonnes annually in 1991 to 8,500 tonnes annually in 1999.<ref>, study for the Swiss National Science Foundation, 2007, page 23</ref> As of 2007, "there should be no current production of C-PentaBDE in Europe, Japan, Canada, Australia and the US"; however, it is possible that production continues elsewhere in the world.<ref name=UNEP2007/>

Commercial pentaBDE is most commonly used as a flame retardant in flexible ] foam; it was also used in ]s in Asia, and in other applications.<ref name=UNEP2007/> The annual demand worldwide was estimated as 7,500 ]s in 2001, of which the Americas accounted for 7,100 tonnes, Europe 150 tonnes, and Asia 150 tonnes.<ref>Bromine Science and Environmental Forum. 21 January 2003.</ref> The global industrial demand increased from 4,000 tonnes annually in 1991 to 8,500 tonnes annually in 1999.<ref>, study for the Swiss National Science Foundation, 2007, page 23</ref> As of 2007, "there should be no current production of C-PentaBDE in Europe, Japan, Canada, Australia and the US"; however, it is possible that production continues elsewhere in the world.<ref name=UNEP2007/>


==Environmental chemistry== ==Environmental chemistry==
PentaBDE is released by different processes into the environment, such as emissions from manufacture of pentaBDE-containing products and from the products themselves.<ref name=UNEP2007/> Elevated concentrations can be found in air, water, soil, food, ], ], and ].<ref name=UNEP2007/><ref>Hale RC, La Guardia MJ, Harvey E, Gaylor MO, Mainor TM (2006): Brominated flame retardant concentrations and trends in abiotic media. Chemosphere. 64(2):181-6. {{DOI|10.1016/j.chemosphere.2005.12.006}} PMID 16434082</ref><ref name=Stapleton2004>Stapleton, Heather M., et al. ''Environmental Science & Technology'' 39(4), 925-931, 2005.</ref> PentaBDE is released by different processes into the environment, such as emissions from manufacture of pentaBDE-containing products and from the products themselves.<ref name=UNEP2007/> Elevated concentrations can be found in air, water, soil, food, ], ], and ].<ref name=UNEP2007/><ref>Hale RC, La Guardia MJ, Harvey E, Gaylor MO, Mainor TM (2006): Brominated flame retardant concentrations and trends in abiotic media. Chemosphere. 64(2):181-6. {{doi|10.1016/j.chemosphere.2005.12.006}} {{PMID|16434082}}</ref><ref name=Stapleton2004>Stapleton, Heather M., et al. Polybrominated Diphenyl Ethers in House Dust and Clothes Dryer Lint.] ''Environmental Science & Technology'' 39(4), 925-931, 2005. {{doi|10.1021/es0486824}}</ref>


==Exposures and health effects== ==Exposures and health effects==
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==Voluntary and governmental actions== ==Voluntary and governmental actions==
In ], industrial users of pentaBDE "agreed to a voluntary phaseout in 1986."<ref name=Alcock2006>Alcock, R. E. and J. Busby (2006): Risk migration and scientific advance: The case of flame-retardant compounds. Risk Analysis 26(2): 369-381. {{DOI|10.1111/j.1539-6924.2006.00739.x}} PMID 16573627</ref> In ], the government "phase out the production and use of the compounds by 1999 and a total ban on imports came into effect within just a few years."<ref name=Alcock2006/> The ] (EU) has carried out a comprehensive risk assessment under the Existing Substances Regulation 793/93/EEC<ref name=EU2001> Luxembourg: Office for Official Publications of the European Communities, 2001. Publication EUR 19730 EN. ISBN 9289404795</ref>; as a consequence, the EU has banned the use of pentaBDE since 2004.<ref name=EU2004> ''Official Journal of the European Union'' 15.2.2003.</ref> In ], industrial users of pentaBDE "agreed to a voluntary phaseout in 1986."<ref name=Alcock2006>Alcock, R. E. and J. Busby (2006): Risk migration and scientific advance: The case of flame-retardant compounds. Risk Analysis 26(2): 369-381. {{doi|10.1111/j.1539-6924.2006.00739.x}} {{PMID|16573627}}</ref> In ], the government "phase out the production and use of the compounds by 1999 and a total ban on imports came into effect within just a few years."<ref name=Alcock2006/> The ] (EU) has carried out a comprehensive risk assessment under the Existing Substances Regulation 793/93/EEC;<ref name=EU2001> {{webarchive|url=https://web.archive.org/web/20070317015559/http://ecb.jrc.it/DOCUMENTS/Existing-Chemicals/RISK_ASSESSMENT/REPORT/penta_bdpereport015.pdf |date=2007-03-17 }} Luxembourg: Office for Official Publications of the European Communities, 2001. Publication EUR 19730 EN. {{ISBN|92-894-0479-5}}</ref> as a consequence, the EU has banned the use of pentaBDE since 2004.<ref name=EU2004> ''Official Journal of the European Union'' 15.2.2003.</ref>


In the ], as of 2005, "no new manufacture or import of" pentaBDE and octaBDE "can occur... without first being subject to EPA ] ] evaluation."<ref name=EPAWeb>U.S. Environmental Protection Agency. "Last updated on Thursday, August 2nd, 2007." Accessed 2007-10-26.</ref> As of mid-2007, a total of eleven states in the U.S. had banned pentaBDE.<ref name=NCEL2007> Washington, DC: National Caucus of Environmental Legislators, June 18, 2007.</ref> In the ], as of 2005, "no new manufacture or import of" pentaBDE and octaBDE "can occur... without first being subject to EPA ] ] evaluation."<ref name=EPAWeb>U.S. Environmental Protection Agency. "Last updated on Thursday, August 2nd, 2007." Accessed 2007-10-26.</ref> As of mid-2007, a total of eleven states in the U.S. had banned pentaBDE.<ref name=NCEL2007> {{webarchive|url=https://web.archive.org/web/20070802103637/http://ncel.net/newsmanager/news_article.cgi?news_id=175 |date=2007-08-02 }} Washington, DC: National Caucus of Environmental Legislators, June 18, 2007.</ref>


It has been proposed that pentaBDE be added to the ] as it meets the criteria for the so-called ]s of persistence, ] and ].<ref name=UNEP2007/> In May 2009, pentaBDE was added to the ] as it meets the criteria for the so-called ]s of persistence, ] and ].


==Alternatives== ==Alternatives==
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