2,8-Dibromodibenzofuran

HCID 82290

Basic information

CAS
10016-52-1
Standard SMILES
Brc1ccc2oc3ccc(Br)cc3c2c1
InChIKey
UFCZRCPQBWIXTR-UHFFFAOYSA-N
Molecular formula
C12H6Br2O
Average molar mass
325.98 g/mol
Monoisotopic mass
323.87853901

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
2,8-Dibromodibenzofuran
IUPAC
2,8-dibromodibenzofuran
English name
2,8-Dibromodibenzofuran
Molecular formula
C12H6Br2O
Molecular weight
325.98

Names & synonyms

2,8-Dibromodibenzofuran2,8-Dibromodibenzo[b,d]furanDibenzofuran, 2,8-dibromo-DTXSID401429932,8-Dibromodibenzo(b,d)furan4,12-dibromo-8-oxatricyclo(7.4.0.02,7)trideca-1(13),2,4,6,9,11-hexaene4,12-dibromo-8-oxatricyclo[7.4.0.02,7]trideca-1(13),2,4,6,9,11-hexaeneRefChem:83571DTXCID0065484634-508-4UFCZRCPQBWIXTR-UHFFFAOYSA-N10016-52-1
Show more names
2,8-dibromo-8-DIBROMODIBENZOFURAN2,8-Dibromodibenzofura2,8-dibrimodibenzofuran2,8-Dibrom-dibenzofuran2,8-dibroMo dibeozofuran2,8-Dibromodibenzofuran>,8-Dibromodibenzo[b,d]furan
2,8-dibromo dibenzofuranMFCD00093683SCHEMBL2586892,8-Dibromodibenzo[b,d]furan #AKOS022172003CS-W009866SY031564EN300-717281

Database identifiers

CAS
10016-52-1
PubChem CID
82290
DTXSID
DTXSID40142993
EC Number
634-508-4
Nikkaji
J1.556.129G

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

Experimental & physicochemical properties

Collision Cross Section148.4 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs]

Physicochemical properties

Melting point
226 ℃ · 226℃
Boiling point
396 ℃ · 396℃
Density
1.886 · 1.886
Flash point
193 ℃ · 193℃
storage temp.
Sealed in dry,Room Temperature
form
powder to crystal

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (97.5%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P264+P265, P270, P273, P280, P301+P316, P305+P351+P338, P321, P330, P337+P317, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (97.5%)

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.

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)

Safety data

hs_code
2932.99.7000
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302-H319-H413
Precautionary statements
P501-P273-P270-P264-P280-P337+P313-P305+P351+P338-P301+P312+P330

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)

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京凯美西化工有限公司02558748998 18951874644 · [email protected]
南京予善化工有限公司025-025-85281586 +86-18105181009

Related reactions

9 records

Compound notes

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