Basic information
- CAS
107555-93-1- Standard SMILES
Brc1cc2oc3cc(Br)c(Br)c(Br)c3c2cc1Br- InChIKey
QMKPILUKNSMQTD-UHFFFAOYSA-N- Molecular formula
- C12H3Br5O
- Average molar mass
- 562.7 g/mol
- Monoisotopic mass
- 557.61008
Overview
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)
Names & identifiers
- Preferred name
- 1,2,3,7,8-Pentabromodibenzofuran
- IUPAC
- 1,2,3,7,8-pentabromodibenzofuran
- English name
- 1,2,3,7,8-PENTABROMODIBENZOFURAN
- Molecular formula
- C12H3Br5O
- Molecular weight
- 562.67
Names & synonyms
1,2,3,7,8-Pentabromodibenzofuran107555-93-1Dibenzofuran, 1,2,3,7,8-pentabromo-1,2,3,7,8-PeBDF25VK3J89H61,2,3,7,8-pentabromo-dibenzofuranDibenzofuran, 1,2,3,7,8-pentabromo3,4,5,11,12-pentabromo-8-oxatricyclo(7.4.0.02,7)trideca-1(13),2,4,6,9,11-hexaene3,4,5,11,12-pentabromo-8-oxatricyclo[7.4.0.02,7]trideca-1(13),2,4,6,9,11-hexaeneRefChem:71371QMKPILUKNSMQTD-UHFFFAOYSA-NDibenzofuran,1,2,3,7,8-pentabromo-
Show more names
UNII-25VK3J89H6DTXSID608694781,2,3,7,8-pentabromodibenzo[b,d]furanDB-250005NS00001556
Database identifiers
- CAS
107555-93-1- PubChem CID
- 86281
- DTXSID
DTXSID60869478- UNII
- 25VK3J89H6
- Nikkaji
- J398.997F
Properties
Computed structural properties
- XLogP
- 7.1
- Topological polar surface area
- 13.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 328
Experimental & physicochemical properties
LogP7.2
Collision Cross Section171.6 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs]
Physicochemical properties
- Boiling point
- 251 °C · 251°C (rough estimate)
- Density
- 2.5167 · 2.5167 (rough estimate)
- refractive index
- 1.5 · 1.5000 (estimate)
- FDA UNII
- 25 VK3J89H6 · 25VK3J89H6
- EPA Substance Registry System
- 1 · 1,2,3,7,8-Pentabromodibenzofuran (107555-93-1)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Treatment
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
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
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.
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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)
Uses & manufacturing
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)
Applications
Uses1,2,3,7,8-Pentabromodibenzofuran is a standard for environmental testing and research. Substance for the analytical method for the detection of PBDD/DF in environmental samples.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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