Dibenzothiophene

Dibenzothiophene

Names
Preferred IUPAC name Dibenzo[b,d]thiophene
Other names Diphenylene sulfide, DBT
Identifiers
CAS Number	132-65-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:23681 Y
ChEMBL	ChEMBL219828 Y
ChemSpider	2915 Y
ECHA InfoCard	100.004.613
EC Number	205-072-9
KEGG	D03777 Y
PubChem CID	3023
RTECS number	HQ3490550
UNII	Z3D4AJ1R48 Y
CompTox Dashboard (EPA)	DTXSID0047741
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
SMILES c1ccc2c(c1)c3ccccc3s2
Properties
Chemical 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
Main hazards	flammable
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H311, H315, H331, H332, H410
Precautionary statements	P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P311, P312, P321, P322, P330, P332+P313, P361, P362, P363, P391, P403+P233, P405, P501
Related compounds
Related compounds	Thiophene Anthracene Benzothiophene Dibenzofuran
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

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[]

Dibenzothiophene is prepared by the reaction of biphenyl with sulfur dichloride in the presence of aluminium chloride.^[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 butyllithium, this heterocycle undergoes stepwise lithiation at the 4- and 6- positions.

References[]