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1,2,3,7,8-Pentachlorodibenzofuran

PubChem CID
42138
Structure
1,2,3,7,8-Pentachlorodibenzofuran_small.png
1,2,3,7,8-Pentachlorodibenzofuran_3D_Structure.png
Molecular Formula
Synonyms
  • 1,2,3,7,8-PENTACHLORODIBENZOFURAN
  • 57117-41-6
  • 1,2,3,7,8-PeCDF
  • Dibenzofuran, 1,2,3,7,8-pentachloro-
  • PCDF 94
Molecular Weight
340.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-18
Description
1,2,3,7,8-Pentachlorodibenzofuran is a polychlorinated dibenzofuran.
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)
L952: Wikipedia. Dibenzofuran. Last Updated 1 June 2009. http://en.wikipedia.org/wiki/Dibenzofuran

1 Structures

1.1 2D Structure

Chemical Structure Depiction
1,2,3,7,8-Pentachlorodibenzofuran.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,2,3,7,8-pentachlorodibenzofuran
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C12H3Cl5O/c13-5-1-4-8(2-6(5)14)18-9-3-7(15)11(16)12(17)10(4)9/h1-3H
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

SBMIVUVRFPGOEB-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=C2C(=CC(=C1Cl)Cl)OC3=CC(=C(C(=C23)Cl)Cl)Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C12H3Cl5O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 KEGG ID

2.3.9 Nikkaji Number

2.3.10 Pharos Ligand ID

2.3.11 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1,2,3,7,8-PCDBF
  • 1,2,3,7,8-pentachlorodibenzofuran
  • 1,2,3,7,8-pentachlorodibenzofuran, 13-12C-labeled

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
340.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
6.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
339.859703 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
337.862653 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
13.1 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
18
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
328
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Collision Cross Section

159.5 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs]
S116 | REFCCS | Collision Cross Section (CCS) Values from Literature | DOI:10.5281/zenodo.10932895

3.2.2 Kovats Retention Index

Semi-standard non-polar
2496 , 2511 , 2549 , 2507 , 2507

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 4
View All
NIST Number
291895
Library
Main library
Total Peaks
121
m/z Top Peak
340
m/z 2nd Highest
342
m/z 3rd Highest
338
Thumbnail
Thumbnail
2 of 4
View All
NIST Number
97227
Library
Replicate library
Total Peaks
184
m/z Top Peak
340
m/z 2nd Highest
338
m/z 3rd Highest
170
Thumbnail
Thumbnail

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 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)
L952: Wikipedia. Dibenzofuran. Last Updated 1 June 2009. http://en.wikipedia.org/wiki/Dibenzofuran

8 Use and Manufacturing

8.1 Uses

CDFs 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)
L952: Wikipedia. Dibenzofuran. Last Updated 1 June 2009. http://en.wikipedia.org/wiki/Dibenzofuran

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Irritant
Health Hazard
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H341 (100%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P203, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P304+P340, P305+P351+P338, P318, P319, P321, P330, P337+P317, P391, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Acute Tox. 3 (100%)

Eye Irrit. 2 (100%)

STOT SE 3 (100%)

Muta. 2 (100%)

Aquatic Acute 1 (100%)

Aquatic Chronic 1 (100%)

9.2 Regulatory Information

California Safe Cosmetics Program (CSCP) Reportable Ingredient

Hazard Traits - Bioaccumulation; Carcinogenicity; Dermatotoxicity; Developmental Toxicity; Endocrine Toxicity; Environmental Persistence; Environmental tox; Hematotoxicity; Hepatotoxicity and Digestive System Toxicity; Reproductive Toxicity

Authoritative List - CA TACs; CWA 303(d); OEHHA RELs; WA PBTs

Report - if used as a fragrance or flavor ingredient

10 Toxicity

10.1 Toxicological Information

10.1.1 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.

10.1.2 RAIS Toxicity Values

Inhalation Unit Risk (IUR) (ug/m^3)^-1
1.1399999999999999
Inhalation Unit Risk Reference
WHO/TEF
Inhalation Chronic Reference Concentration (RfC) (mg/m^3)
1.33333333333333e-06
Inhalation Chronic Reference Concentration Reference
WHO/TEF
Oral Chronic Reference Dose (RfDoc) (mg/kg-day)
2.33333333333333e-08
Oral Chronic Reference Dose Reference
WHO/TEF
Oral Subchronic Chronic Reference Dose (RfDos) (mg/kg-day)
7e-06
Oral Subchronic Chronic Reference Dose Reference
ATSDR Final
Short-term Oral Reference Dose (RfDot) (mg/kg-day)
7e-06
Short-term Oral Reference Dose Reference
ATSDR Final
Oral Slope Factor (CSFo)(mg/kg-day)^-1
3900
Oral Slope Factor Reference
WHO/TEF

10.1.3 Carcinogen Classification

Carcinogen Classification
3, not classifiable as to its carcinogenicity to humans. (L135)

10.1.4 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)
L952: Wikipedia. Dibenzofuran. Last Updated 1 June 2009. http://en.wikipedia.org/wiki/Dibenzofuran

10.1.5 Exposure Routes

Inhalation (L952) ; dermal (L952) ; oral (L952)
L952: Wikipedia. Dibenzofuran. Last Updated 1 June 2009. http://en.wikipedia.org/wiki/Dibenzofuran

10.1.6 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)
L952: Wikipedia. Dibenzofuran. Last Updated 1 June 2009. http://en.wikipedia.org/wiki/Dibenzofuran

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Chemical Co-Occurrences in Literature

12.5 Chemical-Gene Co-Occurrences in Literature

12.6 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 KEGG: EDC

16.4 ChemIDplus

16.5 CAMEO Chemicals

16.6 ChEMBL Target Tree

16.7 UN GHS Classification

16.8 NORMAN Suspect List Exchange Classification

16.9 EPA DSSTox Classification

16.10 EPA Substance Registry Services Tree

16.11 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. California Safe Cosmetics Program (CSCP) Product Database
    1,2,3,7,8-Pentachlorodibenzo-p-furan (1,2,3,7,8_PeCDF)
    https://www.cdph.ca.gov/Programs/CCDPHP/DEODC/OHB/CSCP/Pages/About-CSCP.aspx
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. EPA DSSTox
    1,2,3,7,8-Pentachlorodibenzofuran
    https://comptox.epa.gov/dashboard/DTXSID7052234
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Risk Assessment Information System (RAIS)
    LICENSE
    This work has been sponsored by the U.S. Department of Energy (DOE), Office of Environmental Management, Oak Ridge Operations (ORO) Office through a joint collaboration between United Cleanup Oak Ridge LLC (UCOR), Oak Ridge National Laboratory (ORNL), and The University of Tennessee, Ecology and Evolutionary Biology, The Institute for Environmental Modeling (TIEM). All rights reserved.
    https://rais.ornl.gov/
  8. ChEBI
  9. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
    1,2,3,7,8-Pentachlorodibenzofuran
    http://www.t3db.ca/toxins/T3D2165
  10. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  11. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  12. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
    1,2,3,7,8-Pentachlorodibenzofuran
    http://www.hmdb.ca/metabolites/HMDB0244137
  13. Japan Chemical Substance Dictionary (Nikkaji)
  14. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  15. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    1,2,3,7,8-Pentachlorodibenzofuran
    http://www.nist.gov/srd/nist1a.cfm
  16. SpectraBase
    1,2,3,7,8-Pentachlorodibenzofuran
    https://spectrabase.com/spectrum/COR80py086l
    1,2,3,7,8-Pentachlorodibenzofuran
    https://spectrabase.com/spectrum/AdITz5JcwN0
  17. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    1,2,3,7,8-Pentachlorodibenzofuran
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  18. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
    1,2,3,7,8-Pentachloro-dibenzofuran
    https://pharos.nih.gov/ligands/YUCDB7ZUCVGW
  19. Springer Nature
  20. SpringerMaterials
  21. Wikidata
    1,2,3,7,8-pentachlorodibenzofuran
    https://www.wikidata.org/wiki/Q27155429
  22. PubChem
  23. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    1,2,3,7,8-pentachlorodibenzofuran
    https://www.ncbi.nlm.nih.gov/mesh/67057584
  24. GHS Classification (UNECE)
  25. CAMEO Chemicals
    LICENSE
    CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data.
    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  26. EPA Substance Registry Services
  27. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  28. PATENTSCOPE (WIPO)
CONTENTS