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Dibenzofuran, 2,7-dibromo-

HCID 47643
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
65489-80-7
Standard SMILES
Brc1ccc2c(c1)oc1ccc(Br)cc12
InChIKey
VRGIPEHRKNLRIY-UHFFFAOYSA-N
Molecular formula
C12H6Br2O
Average molar mass
325.98 g/mol
Monoisotopic mass
323.87854

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
Dibenzofuran, 2,7-dibromo-
IUPAC
2,7-dibromodibenzofuran
English name
2,7-Dibromodibenzofuran
Molecular formula
C12H6Br2O
Molecular weight
325.98

Names & synonyms

65489-80-7Dibenzofuran, 2,7-dibromo-DTXSID10215800RefChem:1083366DTXCID001382912,7-DIBROMODIBENZOFURAN2,7-Dibromodibenzo[b,d]furan2,7-dibromo-dibenzofuranSCHEMBL3771900SCHEMBL30693959VRGIPEHRKNLRIY-UHFFFAOYSA-NDB-364435
Show more names
Dibromofunan2,7-dibromodibenofuran
NS00126098

Database identifiers

CAS
65489-80-7
PubChem CID
47643
DTXSID
DTXSID10215800
Nikkaji
J584.178J

Properties

Computed structural properties

XLogP
5.8
Topological polar surface area
13.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
15
Formal charge
0
Complexity
246

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 · 1 item

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 item

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 item

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 · 1 item

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)

Suppliers5 total

Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
HANGZHOU LEAP CHEM CO., LTD.+86-571-87711850 +86-15355479329 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
Beijing Green Guardee Technology Co., Ltd86-010-69706062 · [email protected]
Richest Group Ltd18017061086 · [email protected]

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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 ClassificationNo indication of carcinogenicity (not listed by IARC). (L135)