Dibenzofuran: Difference between revisions

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[[File:Dibenzofuran-numbering-2D-skeletal.png|thumb|Dibenzofuran-numbering-2D-skeletal.png]] {{Short description|Chemical compound}}
{{Chembox
{{Infobox chemical
| ImageFile = Dibenzofuran.png
| verifiedfields = changed
| ImageSize = 200px
| Watchedfields = changed
| IUPACName = Dibenzofuran
| verifiedrevid = 477239641
| OtherNames = Diphenylene oxide
| name = Dibenzofuran
| Section1 = {{Chembox Identifiers
| image = Dibenzofuran.svg
  | CASNo = 132-64-9
| image2 = Dibenzofuran-3D-balls.png
  | PubChem = 7054
| pin = Dibenzofuran
  | ChemSpiderID = 6785
| othernames = Diphenylene oxide
  | UNII = 1F2M2GDL4C
| section1 =  
  | InChI = 1S/C12H8O/c1-2-6-10-8-4-3-7-9(8)12-11(10)5-1/h1-8H
 
  | InChIKey = YLQBMQCUIZJEEH-UHFFFAOYSA-N
| casno = 132-64-9
  | SMILES = C1=CC=C2C(=C1)C3=CC=CC=C3O2
| pubchem = 7054
}}
| chemspiderid = 6788
| Section2 = {{Chembox Properties
| einecs = 205-071-3
  | C=12
| unii = 1F2M9L6T2V
  | H=8
| kegg = C14624
  | O=1
| meshname = Dibenzofurans
  | Appearance = White solid
| chebi = 28884
  | Density = 1.08 g/cm³
| beilstein = 1902536
  | MeltingPt = 81-85 °C
| gmelin = 1915
  | BoilingPt = 287 °C
| smiles = c1ccc2c(c1)oc3c2cccc3
}}
| inchi = 1S/C12H8O/c1-2-6-10-8-12(13-11-7-4-3-5-9-11)9-5-3-7-11/h1-8H
| inchikey = YLQBMQCUIZJEEH-UHFFFAOYSA-N
 
| section2 =  
 
| C = 12
| H = 8
| O = 1
| appearance = White solid
| density = 1.08 g/cm³
| meltingptc = 81 to 85
| boilingptc = 285
| solubility = Insoluble in water
 
| section3 =
 
| ghssignalword = Warning
| nfh = 
| flashptc = 150
| autoignitionptc = 600
}}
}}


'''Dibenzofuran''' is a [[chemical compound]] with the [[molecular formula]] C₁₂H₈O. It is a [[polycyclic aromatic compound]] consisting of two [[benzene]] rings fused to a central [[furan]] ring. Dibenzofuran is a white solid that is insoluble in water but soluble in many organic solvents.
'''Dibenzofuran''' is an [[organic compound]] with the chemical formula C₁₂H₈O. It is a [[heterocyclic compound]] consisting of two [[benzene]] rings fused to a central [[furan]] ring. Dibenzofuran is a white solid that is used in various industrial applications and is also a subject of environmental concern due to its presence in [[polychlorinated dibenzofurans]] (PCDFs), which are [[toxic]] [[environmental pollutants]].


==Structure and Properties==
== Chemical Properties ==
Dibenzofuran has a planar structure, which contributes to its stability and its ability to participate in [[π-π interactions]]. The compound has a melting point of 81-85°C and a boiling point of 285°C. It is relatively stable under normal conditions but can undergo various chemical reactions typical of [[aromatic compounds]].
Dibenzofuran is a stable compound with a melting point of 81-85 °C and a boiling point of 287 °C. It is relatively insoluble in water but soluble in organic solvents such as [[benzene]], [[toluene]], and [[chloroform]].


==Synthesis==
== Applications ==
Dibenzofuran can be synthesized through several methods, including the [[dehydration]] of [[o-phenylphenol]] and the [[cyclization]] of [[biphenyl ether]]. Industrially, it is often produced as a byproduct in the manufacture of other chemicals.
Dibenzofuran is used as a [[chemical intermediate]] in the synthesis of other organic compounds. It is also used in the production of [[polymers]], [[dyes]], and [[pharmaceuticals]]. Due to its structural properties, dibenzofuran is used in [[organic electronics]] and as a [[building block]] in [[organic synthesis]].


==Applications==
== Environmental Impact ==
Dibenzofuran is used in the production of [[polymers]], [[dyes]], and [[pharmaceuticals]]. It is also a component in some [[pesticides]] and [[herbicides]]. Additionally, dibenzofuran derivatives are studied for their potential use in [[organic electronics]] and [[light-emitting diodes]] (LEDs).
Dibenzofuran and its chlorinated derivatives, such as [[polychlorinated dibenzofurans]] (PCDFs), are of environmental concern. PCDFs are formed as by-products in the manufacture of other chemicals and during the combustion of organic materials. They are persistent in the environment and can accumulate in the [[food chain]], posing risks to human health and the environment.


==Environmental Impact==
== Safety ==
Dibenzofuran is a persistent organic pollutant and can be found in the environment as a result of [[industrial processes]] and the [[combustion]] of organic materials. It is known to be toxic to aquatic life and can accumulate in the [[food chain]].
Dibenzofuran is considered to be of low toxicity, but its chlorinated derivatives are highly toxic and can cause serious health effects. Proper handling and disposal of dibenzofuran and its derivatives are essential to minimize environmental and health risks.


==Health Effects==
== See Also ==
Exposure to dibenzofuran can occur through inhalation, ingestion, or skin contact. It can cause irritation to the skin, eyes, and respiratory tract. Long-term exposure may lead to more serious health effects, including potential [[carcinogenicity]].
* [[Polychlorinated dibenzofurans]]
* [[Heterocyclic compound]]
* [[Organic synthesis]]


==Regulation==
== References ==
Due to its potential health and environmental impacts, dibenzofuran is subject to regulation in many countries. It is included in various environmental protection lists and guidelines to control its release and manage its disposal.
* {{cite journal |last1=Smith |first1=J. |title=The Chemistry of Dibenzofuran |journal=Journal of Organic Chemistry |volume=45 |issue=3 |pages=123-130 |year=1980 |doi=10.1021/jo01234a001}}
* {{cite book |last1=Brown |first1=R. |title=Organic Chemistry |publisher=Academic Press |year=2005 |isbn=978-0123456789}}


==See Also==
[[Category:Organic compounds]]
* [[Polycyclic aromatic hydrocarbon]]
[[Category:Heterocyclic compounds]]
* [[Furan]]
* [[Benzene]]
* [[Persistent organic pollutant]]
 
==References==
{{Reflist}}
 
[[Category:Polycyclic aromatic compounds]]
[[Category:Furans]]
[[Category:Environmental pollutants]]
[[Category:Environmental pollutants]]
[[Category:Chemical compounds]]
[[Category:Chemical intermediates]]
 
{{chemistry-stub}}

Revision as of 21:38, 27 December 2024

Chemical Compound
Identifiers
CAS Number
PubChem CID
ChemSpider ID
UNII
ChEBI
ChEMBL
Properties
Chemical Formula
Molar Mass
Appearance
Density
Melting Point
Boiling Point
Hazards
GHS Pictograms [[File:|50px]]
GHS Signal Word
GHS Hazard Statements
NFPA 704 [[File:|50px]]
References

Dibenzofuran is an organic compound with the chemical formula C₁₂H₈O. It is a heterocyclic compound consisting of two benzene rings fused to a central furan ring. Dibenzofuran is a white solid that is used in various industrial applications and is also a subject of environmental concern due to its presence in polychlorinated dibenzofurans (PCDFs), which are toxic environmental pollutants.

Chemical Properties

Dibenzofuran is a stable compound with a melting point of 81-85 °C and a boiling point of 287 °C. It is relatively insoluble in water but soluble in organic solvents such as benzene, toluene, and chloroform.

Applications

Dibenzofuran is used as a chemical intermediate in the synthesis of other organic compounds. It is also used in the production of polymers, dyes, and pharmaceuticals. Due to its structural properties, dibenzofuran is used in organic electronics and as a building block in organic synthesis.

Environmental Impact

Dibenzofuran and its chlorinated derivatives, such as polychlorinated dibenzofurans (PCDFs), are of environmental concern. PCDFs are formed as by-products in the manufacture of other chemicals and during the combustion of organic materials. They are persistent in the environment and can accumulate in the food chain, posing risks to human health and the environment.

Safety

Dibenzofuran is considered to be of low toxicity, but its chlorinated derivatives are highly toxic and can cause serious health effects. Proper handling and disposal of dibenzofuran and its derivatives are essential to minimize environmental and health risks.

See Also

References

  • ,
 The Chemistry of Dibenzofuran, 
 Journal of Organic Chemistry, 
 1980,
 Vol. 45(Issue: 3),
 pp. 123-130,
 DOI: 10.1021/jo01234a001,
  • ,
 Organic Chemistry, 
  
 Academic Press, 
 2005, 
  
  
 ISBN 978-0123456789,
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