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2,3,4,7,8-Pentabromodibenzofuran

HCID 107998
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
13116-92-2
Standard-SMILES
Brc1cc2oc3c(Br)c(Br)c(Br)cc3c2cc1Br
InChIKey
KHQDJFUIVSESDP-UHFFFAOYSA-N
Summenformel
C12H3Br5O
Durchschnittliche Molmasse
562,7 g/mol
Monoisotopische Masse
557,61008

Überblick

Chlorinated dibenzofurans (CDFs) are a family of chemical that contain one to eight chlorine atoms attached to the carbon atoms of the parent chemical, dibenzofuran. The CDF family contains 135 individual compounds (known as congeners) with varying harmful health and environmental effects. Of these 135 compounds, those that contain chlorine atoms at the 2,3,7,8-positions of the parent dibenzofuran molecule are especially harmful. Other than for laboratory use of small amounts of CDFs for research and development purposes, these chemicals are not deliberately produced by industry. Most CDFs are produced in very small amounts as unwanted impurities of certain products and processes utilizing chlorinated compounds. Only a few of the 135 CDF compounds have been produced in large enough quantities so that their properties, such as color, smell, taste, and toxicity could be studied. (L952)

Namen und Bezeichner

Bevorzugter Name
2,3,4,7,8-Pentabromodibenzofuran
IUPAC
2,3,4,7,8-pentabromodibenzofuran
Englischer Name
2,3,4,7,8-PENTABROMODIBENZOFURAN
Summenformel
C12H3Br5O
Molmasse
562.67

Namen und Synonyme

2,3,4,7,8-PentabromodibenzofuranDibenzofuran, 2,3,4,7,8-pentabromo-7HQ7YK2A7M2,3,4,7,8-pentabromo-dibenzofuranDTXSID507387013116-92-24,5,6,11,12-pentabromo-8-oxatricyclo(7.4.0.02,7)trideca-1(13),2,4,6,9,11-hexaene4,5,6,11,12-pentabromo-8-oxatricyclo[7.4.0.02,7]trideca-1(13),2,4,6,9,11-hexaeneRefChem:81289DTXCID8034031KHQDJFUIVSESDP-UHFFFAOYSA-N131166-92-2
Weitere Namen anzeigen
UNII-7HQ7YK2A7M2,3,4,7,8-Pentabromodibenzo[b,d]furanDB-250825NS00122840

Datenbank-Bezeichner

CAS
13116-92-2、131166-92-2
PubChem CID
107998
DTXSID
DTXSID5073870
UNII
7HQ7YK2A7M
Nikkaji
J776.183J

Eigenschaften

Berechnete Struktureigenschaften

XLogP
7,2
Polarare Oberfläche (TPSA)
13,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
18
Formalladung
0
Komplexität
328

Experimentelle und physikochemische Eigenschaften

LogP7.04
Collision Cross Section173.6 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs]

Physikochemische Eigenschaften

EPA chemische Informationen
2 · 2,3,4,7,8-Pentabromodibenzofuran (131166-92-2)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Toxikologische Informationen

Treatment · 1 Eintrag

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health Effects · 1 Eintrag

CDFs cause vomiting and diarrhea, anemia, more frequent lung infections, numbness and other effects on the nervous system, and mild changes in the liver. However, there were no permanent liver changes or definite liver damage found in people who ingested CDFs. (L952)

Exposure RoutesInhalation (L952) ; dermal (L952) ; oral (L952)
Toxicity Summary · 1 Eintrag

Halogenated dibenzofurans (PCDFs and PBDFs) bind the aryl hydrocarbon receptor (AhR), which increases its ability to activate transcription in the XRE (xenobiotic resoponse element) promoter region. Specifically AhR binds to the PCDF, translocates it to the nucleus and together with hydrocarbon nuclear translocator (ARNT) and xenobiotic responsive element (XRE) increases the expression of CYP1A1 and aryl hydrocarbon hydroxylase (CYP1B1). AhR signaling also increseases conversion of arachidonic acid to prostanoids via cyclooxygenase-2, alters Wnt/beta-catenin signaling downregulating Sox9 and alters signaling by receptors for inflammatory cytokines. AhR signalling also alters proteasomal degradation of steroid hormone receptors, alters cellular UVB stress response and changes the differentiation of certain T-cell subsets. The resulting AhR mediated activation and alteration leads to body weight loss, cancer and thymic atrophy (characteristic of immune and endocrine disruption) which are common toxic responses to PCDFs and related toxic halogenated aryl hydrocarbons.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

No information on the metabolism of dibenzofuran in mammalian organisms was found in the available literature. The bacteria Sphingomonas, Brevibacterium, Terrabacter, and Staphylococcus auricularis degrade dibenzofuran to 2,2',3-trihydroxybiphenyl via dibenzofuran 4,4a-dioxygenase. (L952)

Verwendung und Herstellung

UsesCDFs are created from production of coal tar and during incineration. They are used as insecticides, in the production of PVC, and in industrial bleaching. (L952)

Anwendungen

Verwenden1,2,3,7,8-Pentabromodibenzofuran is a standard for testing and research. Substance for the analytical detection of PBDD/DF in environmental samples. Toxicity evaluation of brominated and brominated/chlorinated dioxins using CALUX bioassay

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Signs and SymptomsSkin and eye irritations, especially severe acne, darkened skin color, and swollen eyelids with discharge are the most obvious health effects of the CDF poisoning. (L952)
Carcinogen ClassificationNo indication of carcinogenicity (not listed by IARC). (L135)