Dibenzothiophene: Difference between revisions

Dibenzothiophene
Names
	Preferred IUPAC name Dibenzo[b,d]thiophene
	Other names Diphenylene sulfide, DBT
Identifiers
CAS Number	132-65-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:23681 ;
ChEMBL	ChEMBL219828 ;
ChemSpider	2915 ;
ECHA InfoCard	100.004.613
EC Number	205-072-9;
KEGG	D03777 ;
PubChem CID	3023;
RTECS number	HQ3490550;
UNII	Z3D4AJ1R48 ;
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 Key: IYYZUPMFVPLQIF-UHFFFAOYSA-N ; 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
	Occupational safety and health (OHS/OSH):
Main hazards	flammable, toxic
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, 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). verify (what is ?) Infobox references

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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.^[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. With butyllithium, this heterocycle undergoes stepwise lithiation at the 4-position. S-oxidation with peroxides gives the sulfoxide.^[3]

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.^[4]

References

^ Ho, Teh C. (2004). "Deep HDS of Diesel Fuel: Chemistry and Catalysis". Catalysis Today. 98 (1–2): 3–18. doi:10.1016/j.cattod.2004.07.048.
^ Klemm, L. H.; Karchesy, Joseph J. (1978). "The Insertion and Extrusion of Heterosulfur Bridges. VIII. Dibenzothiophene from Biphenyl and Derivatives". Journal of Heterocyclic Chemistry. 15 (4): 561–563. doi:10.1002/jhet.5570150407.
^ Waldecker, Bernd; Kafuta, Kevin; Alcarazo, Manuel (2019). "Preparation of 5-(Triisopropylalkynyl) dibenzo[b,d]thiophenium triflate". Organic Syntheses. 96: 258–276. doi:10.15227/orgsyn.096.0258. S2CID 239319277.
^ Bhanuchandra, M.; Yorimitsu Hideki. "Dibenzothiophene 5,5-dioxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn02046.

[1] Ho, Teh C. (2004). "Deep HDS of Diesel Fuel: Chemistry and Catalysis". Catalysis Today. 98 (1–2): 3–18. doi:10.1016/j.cattod.2004.07.048.

[2] Klemm, L. H.; Karchesy, Joseph J. (1978). "The Insertion and Extrusion of Heterosulfur Bridges. VIII. Dibenzothiophene from Biphenyl and Derivatives". Journal of Heterocyclic Chemistry. 15 (4): 561–563. doi:10.1002/jhet.5570150407.

[3] Waldecker, Bernd; Kafuta, Kevin; Alcarazo, Manuel (2019). "Preparation of 5-(Triisopropylalkynyl) dibenzo[b,d]thiophenium triflate". Organic Syntheses. 96: 258–276. doi:10.15227/orgsyn.096.0258. S2CID 239319277.

[4] Bhanuchandra, M.; Yorimitsu Hideki. "Dibenzothiophene 5,5-dioxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn02046.

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@@ Line 1: / Line 1: @@
-{{chembox
+{{Chembox
+| Watchedfields  = changed
-| verifiedrevid = 289525566
+| verifiedrevid  = 443634616
-|   Name = Dibenzothiophene
-|   ImageFile = Dibenzothiophen - Dibenzothiophene.svg
+| Name           = Dibenzothiophene
+| ImageFile      = Dibenzothiophen - Dibenzothiophene.svg
-| ImageSize = 190px
+| ImageSize      = 190px
-|   ImageName = Skeletal formula
+| ImageAlt       = Skeletal formula of dibenzothiophene
-|   ImageFile1 = Dibenzothiophene-3D-balls.png
+| ImageFile1     = Dibenzothiophene 3D ball.png
-|   ImageSize1 = 230px
+| ImageSize1     = 220px
-|   ImageName1 = Ball-and-stick model
+| ImageAlt1      = Ball-and-stick model of the dibenzothiophene molecule
-|   IUPACName = Dibenzothiophene
+| ImageFile2     = DBTsample.jpg
-|   OtherNames = Diphenylene sulfide, DBT
+| ImageSize2     = 180px
-| Section1 = {{Chembox Identifiers
-|   SMILES =
+| ImageAlt2      = Sample
+| PIN            = Dibenzo[''b'',''d'']thiophene
-|   CASNo_Ref = {{cascite}}
+| 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
+| RTECS = HQ3490550
+| PubChem = 3023
+| EC_number = 205-072-9
   }}
-| Section2 = {{Chembox Properties
+| Section2       = {{Chembox Properties
-|   Formula = C<sub>12</sub>H<sub>8</sub>S
+| Formula = C<sub>12</sub>H<sub>8</sub>S
-|   MolarMass =  184.26 g/mol
+| MolarMass = 184.26 g/mol
-|   Appearance = Colourless crystals
+| Appearance = Colourless crystals
-|   Density = 1.252 g/cm<sup>3</sup>
+| Density = 1.252 g/cm<sup>3</sup>
-|   Solubility = insol.
+| Solubility = insol.
-|   Solvent = other solvents
+| Solvent = other solvents
-|   SolubleOther = [[benzene]] and related
+| SolubleOther = [[benzene]] and related
-|   MeltingPt = 97-100 °C(lit.)
+| MeltingPtC = 97 to 100
+| MeltingPt_notes = (lit.)
-|   BoilingPt = 332-333 °C
-|   pKb =
+| BoilingPtC = 332 to 333
+| BoilingPt_notes =
+| pKb =
   }}
-| Section3 = {{Chembox Structure
+| Section3       = {{Chembox Structure
-|   CrystalStruct =
+| CrystalStruct =
-|   Dipole =
+| Dipole =
   }}
-| Section7 = {{Chembox Hazards
+| Section7       = {{Chembox Hazards
-|   ExternalMSDS =
+| ExternalSDS =
-|   MainHazards = flammable
+| MainHazards = flammable, toxic
-|   FlashPt =
+| FlashPt =
+| GHSPictograms = {{GHS skull and crossbones}}{{GHS exclamation mark}}{{GHS environment}}
-|   RPhrases = 22
-|   SPhrases = 36
+| 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
+| Section8       = {{Chembox Related
-|   OtherCpds = [[Thiophene]]<br />[[anthracene]]<br />[[benzothiophene]]
+| OtherCompounds = [[Thiophene]]<br/>[[Anthracene]]<br/>[[Benzothiophene]]<br/>[[Dibenzofuran]]
   }}
 }}
-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]].<ref>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}}</ref>
+'''Dibenzothiophene''' (DBT, diphenylene [[Sulfide (organic)|sulfide]]) is the [[organosulfur compound]] consisting of two [[benzene ring]]s fused to a central [[thiophene]] ring. It has the chemical formula C<sub>12</sub>H<sub>8</sub>S. It is a colourless solid that is chemically somewhat similar to [[anthracene]]. This [[tricyclic]] [[heterocyclic compound|heterocycle]], and especially its disubstituted derivative [[4,6-Dimethyldibenzothiophene|4,6-dimethyldibenzothiophene]] are problematic impurities in [[petroleum]].<ref>{{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 }}</ref>
 ==Synthesis and reactions==
-Dibenzothiophene is prepared by the reaction of [[biphenyl]] with [[sulfur dichloride]] in the presence of [[aluminium trichloride]].<ref>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}}</ref>
+Dibenzothiophene is prepared by the reaction of [[biphenyl]] with [[sulfur dichloride]] in the presence of [[aluminium chloride]].<ref>{{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 }}</ref>
+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]].<ref>{{cite journal |doi=10.15227/orgsyn.096.0258|title=Preparation of 5-(Triisopropylalkynyl) dibenzo&#91;b,d&#93;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 }}</ref>
-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.
+Dibenzothiophene is [[electron-rich]], and naturally undergoes aromatic substitution [[arene substitution patterns|''para'']] to the sulfide.  Oxidation to the sulfoxide or sulfone leaves the compound electron poor, and substitution occurs at the ''meta'' position instead.<ref>{{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}}</ref>
-==References==
-<references/>
+==References==
-[[Category:Dibenzothiophenes]]
+{{Reflist}}
+[[Category:Thiophenes]]
-[[ca:Dibenzotiofè]]
-[[es:Dibenzotiofeno]]
-[[fr:Dibenzothiophène]]
-[[ja:ジベンゾチオフェン]]
-[[pl:Dibenzotiofen]]