Dibenzothiophene

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Dibenzothiophene


IUPAC name Dibenzothiophene
Other names Diphenylene sulfide, DBT
Identifiers
CAS number	132-65-0^Y
ChemSpider	2915^Y
UNII	Z3D4AJ1R48^Y
KEGG	D03777^Y
ChEBI	CHEBI:23681^Y
ChEMBL	CHEMBL219828^Y
RTECS number	HQ3490550
Jmol-3D images	Image 1
SMILES c1ccc2c(c1)c3ccccc3s2
InChI InChI=1S/C12H8S/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H^Y Key: IYYZUPMFVPLQIF-UHFFFAOYSA-N^Y InChI=1/C12H8S/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H Key: IYYZUPMFVPLQIF-UHFFFAOYAY
Properties
Molecular formula	C₁₂H₈S
Molar mass	184.26 g/mol
Appearance	Colourless crystals
Density	1.252 g/cm³
Melting point	97-100 °C(lit.)
Boiling point	332-333 °C
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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

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

↑ 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
↑ 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

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