Dibenzofuran

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Dibenzofuran
Dibenzofuran-numbering-2D-skeletal.png
Dibenzofuran 3D ball.png
Names
Preferred IUPAC name
Dibenzo[b,d]furan
Identifiers
3D model (JSmol)
3DMet
121100
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.612 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-071-3
67825
KEGG
PubChem CID
UNII
UN number 3077
  • InChI=1S/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H Yes check.svgY
    Key: TXCDCPKCNAJMEE-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H
    Key: TXCDCPKCNAJMEE-UHFFFAOYAX
  • o2c1ccccc1c3c2cccc3
Properties
C12H8O
Molar mass 168.19 g/mol
Appearancewhite crystalline powder
Melting point 81 to 85 °C (178 to 185 °F; 354 to 358 K)
Boiling point 285 °C (545 °F; 558 K)
Insoluble
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H302, H312, H332, H411
P273, P391, P501
Related compounds
Related compounds
Furan
Benzofuran
Dibenzodioxin
Dibenzothiophene
Carbazole
Polyozellin (compound with a kernel with two dibenzofurans that share the same benzene ring)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Dibenzofuran is a heterocyclic organic compound with the chemical structure shown at right. It is an aromatic compound that has two benzene rings fused to a central furan ring. All the numbered carbon atoms have a hydrogen atom bonded to each of them. It is a volatile white solid that is soluble in nonpolar organic solvents. It is obtained from coal tar, where it exists as a 1% component. [1]

Contents

Reactions

Dibenzofuran is thermally robust with a convenient liquid range. These properties, together with its low toxicity, are exploited by the use of DBF as a heat transfer agent. [1]

It undergoes electrophilic reactions, such as halogenation and Friedel-Crafts reactions. Reaction of DBF with butyl lithium results in dilithiation. [2]

Dibenzofuran is the precursor to the drug furobufen by Friedel-Crafts reaction with succinic anhydride.

Safety

Dibenzofuran is a relatively non-toxic compound as evidenced by rats being unaffected after a 200-day diet consisting of 0.025 – 0.4% of DBF. [1] The polychlorinated dibenzofurans are however among the potentially toxic dioxins and dioxin-like compounds.

Dibenzofuran is cited in the United States Clean Air Act 1990 Amendments -Hazardous Air Pollutants as a volatile hazardous air pollutant of potential concern. The Superfund Amendment Reauthorization Act (SARA) Section 110 placed dibenzofuran on the revised Agency for Toxic Substances and Disease Registry (ATSDR) priority list of hazardous substances to be the subject of a toxicological profile. The listing was based on the substance’s frequency of occurrence at Comprehensive Environmental Response, Compensation, and Liability Act (CERCLA) National Priorities List sites, its toxicity, and/or its potential for human exposure. [3]

See also

Related Research Articles

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<span class="mw-page-title-main">Polychlorinated biphenyl</span> Chemical compound

Polychlorinated biphenyls (PCBs) are highly carcinogenic chemical compounds, formerly used in industrial and consumer products, whose production was banned in the United States by the Toxic Substances Control Act in 1979 and internationally by the Stockholm Convention on Persistent Organic Pollutants in 2001. They are organic chlorine compounds with the formula C12H10−xClx; they were once widely used in the manufacture of carbonless copy paper, as heat transfer fluids, and as dielectric and coolant fluids for electrical equipment.

Polychlorinated dibenzodioxins (PCDDs), or simply dioxins, are a group of long-lived polyhalogenated organic compounds that are primarily anthropogenic, and contribute toxic, persistent organic pollution in the environment.

<span class="mw-page-title-main">Butanone</span> Chemical compound

Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

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<span class="mw-page-title-main">Dibenzo-1,4-dioxin</span> Chemical compound

Dibenzo-1,4-dioxin, also dibenzodioxin or dibenzo-p-dioxin (dibenzo-para-dioxin), is a polycyclic heterocyclic organic compound in which two benzene rings are connected by a 1,4-dioxin ring. Its molecular formula is C12H8O2. The two oxygen atoms occupy opposite (para-) positions in the six-membered dioxin ring.

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Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the "parent" of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants.

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1,4-Dioxin (also referred as dioxin or p-dioxin) is a heterocyclic, organic, non-aromatic compound with the chemical formula C4H4O2. There is an isomeric form of 1,4-dioxin, 1,2-dioxin (or o-dioxin). 1,2-Dioxin is very unstable due to its peroxide-like characteristics.

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References

  1. 1 2 3 Gerd Collin and Hartmut Höke "Benzofurans" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi : 10.1002/14356007.l03_l01
  2. Ulrich Iserloh, Yoji Oderaotoshi, Shuji Kanemasa, and Dennis P. Curran "Synthesis of (R,R)-4,6-Dibenzofurandiyl-2,2'-Bis (4-Phenyloxazoline) (DBFOX/PH) – A Novel Trridentate Ligand" Org. Synth. 2003, volume 80, 46. doi : 10.15227/orgsyn.080.0046
  3. "Archived copy" (PDF). Archived from the original (PDF) on 2012-10-09. Retrieved 2014-03-09.{{cite web}}: CS1 maint: archived copy as title (link)