Dibenzothiophene

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Dibenzothiophene
Skeletal formula of dibenzothiophene
Ball-and-stick model of the dibenzothiophene molecule
Names
IUPAC name
Dibenzothiophene
Other names
Diphenylene sulfide, DBT
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.613
KEGG
RTECS number HQ3490550
UNII
Properties
C12H8S
Molar mass 184.26 g/mol
Appearance Colourless crystals
Density 1.252 g/cm3
Melting point 97 to 100 °C (207 to 212 °F; 370 to 373 K) (lit.)
Boiling point 332 to 333 °C (630 to 631 °F; 605 to 606 K)
insol.
Solubility in other solvents benzene and related
Hazards
Main hazards flammable
R-phrases (outdated) 22
S-phrases (outdated) 36
Related compounds
Related compounds
Thiophene
anthracene
benzothiophene
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

Dibenzothiophene (DBT) is the organosulfur compound consisting of two benzene rings fused to a central thiophene ring. It is a colourless solid that is chemically somewhat similar to anthracene. This tricyclic heterocycle, and especially its alkyl substituted derivatives, occur widely in heavier fractions of petroleum.[1]

Synthesis and reactions[edit]

Dibenzothiophene is prepared by the reaction of biphenyl with sulfur dichloride in the presence of aluminium trichloride.[2]

Reduction with lithium results in scission of one C-S bond. S-oxidation occurs to give the sulfone, which is more labile than the parent dibenzothiophene. With butyl lithium, this heterocycle undergoes stepwise lithiation at the 4- and 6- positions.

References[edit]

  1. ^ Teh C. Ho "Deep HDS of diesel fuel: chemistry and catalysis" Catalysis Today 2004, Volume 98, pp. 3-18. doi:10.1016/j.cattod.2004.07.048
  2. ^ L. H. Klemm, Joseph J. Karchesy "Dibenzothiophene from biphenyl and derivatives" Journal of Heterocyclic Chemistry, 1978, Volume 15 Issue 4, Pages 561 - 563. doi:10.1002/jhet.5570150407