Dibenzothiophene

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Dibenzothiophene
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 132-65-0 YesY
ChemSpider 2915 YesY
UNII Z3D4AJ1R48 YesY
KEGG D03777 YesY
ChEBI CHEBI:23681 YesY
ChEMBL CHEMBL219828 YesY
RTECS number HQ3490550
Jmol-3D images Image 1
Properties
Molecular formula 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)
Solubility in water insol.
Solubility in other solvents benzene and related
Hazards
R-phrases 22
S-phrases 36
Main hazards flammable
Related compounds
Related compounds Thiophene
anthracene
benzothiophene
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Dibenzothiophene 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