Dibenzofuran

Dibenzofuran
Skeletal formula showing numbering convention
Ball-and-stick model of the dibenzofuran molecule
Identifiers
132-64-9 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:28145 YesY
ChEMBL ChEMBL277497 YesY
ChemSpider 551 YesY
ECHA InfoCard 100.004.612
KEGG C07729 YesY
PubChem 568
Properties
C12H8O
Molar mass 168.19 g/mol
Appearance white 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
R-phrases R51/53
S-phrases S24/25 S29 S61
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).
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Infobox references

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 (not shown in the image). 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]

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 bultyl 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 controversial and potentially dangerous.

See also

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
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