Dibenzothiophene

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, 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.

Synthesis and reactions

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

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.