Dibenzofurans

Dibenzofuran
Identifiers


CAS Number	132-64-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28145^Y
ChemSpider	551^Y
ECHA InfoCard	100.004.612
KEGG	C07729^Y
PubChem CID	568
InChI InChI=1S/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H^Y Key: TXCDCPKCNAJMEE-UHFFFAOYSA-N^Y InChI=1/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H Key: TXCDCPKCNAJMEE-UHFFFAOYAX
SMILES o2c1ccccc1c3c2cccc3
Properties
Chemical formula	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)
Solubility in water	Insoluble
Hazards
R-phrases (outdated)	R51/53
S-phrases (outdated)	S24/25 S29 S61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).
Y (what is ^YN ?)
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.

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.

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

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

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. The polychlorinated dibenzofurans are however controversial and potentially dangerous.

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