:Dibenzothiophene
{{Chembox
| Watchedfields = changed
| verifiedrevid = 443634616
| Name = Dibenzothiophene
| ImageFile = Dibenzothiophen - Dibenzothiophene.svg
| ImageSize = 190px
| ImageAlt = Skeletal formula of dibenzothiophene
| ImageFile1 = Dibenzothiophene 3D ball.png
| ImageSize1 = 220px
| ImageAlt1 = Ball-and-stick model of the dibenzothiophene molecule
| ImageFile2 = DBTsample.jpg
| ImageSize2 = 180px
| ImageAlt2 = Sample
| PIN = Dibenzo[b,d]thiophene
| OtherNames = Diphenylene sulfide, DBT
| Section1 = {{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 23681
| SMILES = c1ccc2c(c1)c3ccccc3s2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2915
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Z3D4AJ1R48
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D03777
| InChI = 1/C12H8S/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H
| InChIKey = IYYZUPMFVPLQIF-UHFFFAOYAY
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 219828
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H8S/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IYYZUPMFVPLQIF-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 132-65-0
| RTECS = HQ3490550
| PubChem = 3023
| EC_number = 205-072-9
}}
| Section2 = {{Chembox Properties
| Formula = C12H8S
| MolarMass = 184.26 g/mol
| Appearance = Colourless crystals
| Density = 1.252 g/cm3
| Solubility = insol.
| Solvent = other solvents
| SolubleOther = benzene and related
| MeltingPtC = 97 to 100
| MeltingPt_notes = (lit.)
| BoilingPtC = 332 to 333
| BoilingPt_notes =
| pKb =
}}
| Section3 = {{Chembox Structure
| CrystalStruct =
| Dipole =
}}
| Section7 = {{Chembox Hazards
| ExternalSDS =
| MainHazards = flammable, toxic
| FlashPt =
| GHSPictograms = {{GHS skull and crossbones}}{{GHS exclamation mark}}{{GHS environment}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|302|311|315|331|332|410}}
| PPhrases = {{P-phrases|261|264|270|271|273|280|301+312|302+352|304+312|304+340|311|312|321|322|330|332+313|361|362|363|391|403+233|405|501}}
}}
| Section8 = {{Chembox Related
| OtherCompounds = Thiophene
Anthracene
Benzothiophene
Dibenzofuran
}}
}}
Dibenzothiophene (DBT, diphenylene sulfide) is the organosulfur compound consisting of two benzene rings fused to a central thiophene ring. It has the chemical formula C12H8S. It is a colourless solid that is chemically somewhat similar to anthracene. This tricyclic heterocycle, and especially its disubstituted derivative 4,6-dimethyldibenzothiophene are problematic impurities in petroleum.{{cite journal|doi=10.1016/j.cattod.2004.07.048|title=Deep HDS of Diesel Fuel: Chemistry and Catalysis |year=2004 |last1=Ho |first1=Teh C. |journal=Catalysis Today |volume=98 |issue=1–2 |pages=3–18 }}
Synthesis and reactions
Dibenzothiophene is prepared by the reaction of biphenyl with sulfur dichloride in the presence of aluminium chloride.{{cite journal|doi=10.1002/jhet.5570150407|title=The Insertion and Extrusion of Heterosulfur Bridges. VIII. Dibenzothiophene from Biphenyl and Derivatives |year=1978 |last1=Klemm |first1=L. H. |last2=Karchesy |first2=Joseph J. |journal=Journal of Heterocyclic Chemistry |volume=15 |issue=4 |pages=561–563 }}
Reduction with lithium results in scission of one C-S bond. With butyllithium, this heterocycle undergoes stepwise lithiation at the 4-position. S-oxidation with peroxides gives the sulfoxide.{{cite journal |doi=10.15227/orgsyn.096.0258|title=Preparation of 5-(Triisopropylalkynyl) dibenzo[b,d]thiophenium triflate |year=2019 |last1=Waldecker |first1=Bernd |journal=Organic Syntheses |volume=96 |pages=258–276 |s2cid=239319277|first2= Kevin|last2=Kafuta|first3=Manuel|last3=Alcarazo|doi-access=free }}
Dibenzothiophene is electron-rich, and naturally undergoes aromatic substitution para to the sulfide. Oxidation to the sulfoxide or sulfone leaves the compound electron poor, and substitution occurs at the meta position instead.{{cite encyclopedia|title=Encyclopedia of Reagents for Organic Synthesis|doi=10.1002/047084289X.rn02046|entry=Dibenzothiophene 5,5-dioxide|first1=M.|last1=Bhanuchandra|author2=Yorimitsu Hideki}}
References
{{Reflist}}