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1,2,3,4-Tetrachlorodibenzofuran
Dibenzofuran, 1,2,3,4-tetrachloro · 1,2,3,4-tetrachlorodibenzo[b,d]furan
Identifikatoren & physikalische Daten
| CAS No. | 24478-72-6 |
|---|---|
| Summenformel | C12H4Cl4O |
| Durchschnittliche Molmasse | 306 g/mol |
| Monoisotopische Masse | 303,901626 g/mol |
| SMILES | Clc1c(Cl)c(Cl)c2c(oc3ccccc32)c1Cl |
| InChIKey | AETAPIFVELRIDN-UHFFFAOYSA-N |
| PubChem CID | 35331 |
| DTXSID | DTXSID5067556 |
Chemische & physikalische Eigenschaften
| XLogP | 5,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 13,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 300 |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | 6.17 |
| Schmelzpunkt | 168.75°C |
| Siedepunkt | 440.46°C (rough estimate) |
| Dichte | 1.5600 (estimate) |
| Brechungsindex | 1.7140 (rough estimate) |
| Henry-Konstante | 3.6×10-1 mol/(m3Pa) at 25℃, Govers and Krop (1998) |
Sicherheit & Vorschriften
| Gesundheitliche Auswirkungen | 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) |
|---|---|
| Expositionspfade | Inhalation (L952)dermal (L952)oral (L952) |
| Toxizitätsübersicht | 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. |
| Signs and Symptoms | Skin 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 Classification | 3, not classifiable as to its carcinogenicity to humans. (L135) |
Anwendungen & Verwendung
Verwenden
1,2,3,4-Tetrachlorodibenzofuran is a dioxin-like PCB impurity that is found in some Japanese agrochemical formulations.