diphenyl sulfide
{{Short description|Organic compound}}
{{Chembox
| IUPACName = Phenylsulfanylbenzene
| OtherNames =
| ImageFile = Diphenylsulfane 200.svg
| ImageSize =
| ImageAlt = Diphenyl sulfide molecule
| Section1 = {{Chembox Identifiers
| CASNo = 139-66-2
| Abbreviations = Ph2S
| Beilstein = 1907932
| ChEBI = 38959
| ChEMBL = 219876
| ChemSpiderID = 8436
| EINECS =
| EC_number = 205-371-4
| EC_number_Comment =
| InChI = 1S/C12H10S/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H
| InChIKey = LTYMSROWYAPPGB-UHFFFAOYSA-N
| RTECS =
| SMILES = C1=CC=C(C=C1)SC2=CC=CC=C2
| UNNumber =
| UNII = B5P3Y93MNR
| DTXSID = DTXSID8044383
}}
| Section2 = {{Chembox Properties
| Formula = {{chem2|(C6H5)2S}}
| C=12|H=10|S=1
| Appearance = Colorless liquid
| MeltingPt =
| MeltingPtC = −25.9
| MeltingPt_ref =
| BoilingPtC = 296
| BoilingPt_ref =
| BoilingPt_notes=
| Density = 1.113 g/cm3 (20 °C)
{{Cite book|title= CRC Handbook of Chemistry and Physics |edition=90 |chapter=3 |page=220|year=2010}}
Vapor: 6.42 (air = 1.0)
| Solubility = insoluble
| SolubleOther = Soluble in diethyl ether, benzene, carbon disulfide.
| RefractIndex = 1.6327
| VaporPressure = 0.01 hPa at 25 °C{{cite web | url=https://gestis.dguv.de/data?name=015260&lang=en | title=GESTIS-Stoffdatenbank }}
| Viscosity = {{ubl|Dynamic:|21.45 mPa·s at 20 °C|18.4 mPa·s at 40 °C|Kinematic:|19.43 mm2/s at 20 °C|16.7 mm2/s at 40 °C}}
}}
| Section3 = {{Chembox Structure
| MolShape = Bent on the sulfur atom
}}
| Section7 = {{Chembox Hazards
| Hazards_ref =
| AutoignitionPt =
| ExploLimits =
| FlashPt = {{cvt|113|C|F}}
| LD50 = {{ubl|300 to 2000 mg/kg (oral, female rat)|5000 mg/kg (dermal, female rat)|11300 μL/kg (dermal, rabbit){{cite web |title=Diphenyl sulfide |url=https://pubchem.ncbi.nlm.nih.gov/compound/8766}}|490 μL/kg (oral, rat)|545 mg/kg (oral, rat)|12600 mg/kg (dermal, rabbit)}}
| LC50 =
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-I =
| NFPA-S =
| PEL =
| REL =
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|H302|H315|H319|H410}}
| PPhrases = {{P-phrases|P264|P270|P273|P280|P301+P312|P301+P317|P302+P352|P305+P351+P338|P321|P330|P332+P317|P362+P364|P391|P501}}
}}
| Section9 = {{Chembox Related
| OtherCompounds = {{ubl|Diphenyl ether|Diphenyl selenide|Diphenyl telluride|Diphenyl disulfide|Thiophenol|Diphenyl sulfone}}
}}
}}
Diphenyl sulfide is an organosulfur compound with the chemical formula {{chem2|(C6H5)2S|auto=1}}, often abbreviated as {{chem2|Ph2S}}, where Ph stands for phenyl. It is a colorless liquid with an unpleasant odor. Diphenyl sulfide is an aromatic sulfide. The molecule consists of two phenyl groups attached to a sulfur atom.
Synthesis, reactions, occurrence
Many methods exist for the preparation of diphenyl sulfide. It arises by a Friedel-Crafts-like reaction of sulfur monochloride and benzene.{{cite journal |doi=10.15227/orgsyn.014.0036 |title=Diphenyl Sulfide |journal=Organic Syntheses |date=1934 |volume=14 |page=36|first1=W. W.|last1=Hartman|first2=L. A.|last2=Smith|first3=J. B.|last3=Dickey}} Diphenyl sulfide and its analogues can also be produced by coupling reactions using metal catalysts.{{cite journal |doi=10.1126/science.aam9041 |title=Palladium-catalyzed carbon-sulfur or carbon-phosphorus bond metathesis by reversible arylation |date=2017 |last1=Lian |first1=Zhong |last2=Bhawal |first2=Benjamin N. |last3=Yu |first3=Peng |last4=Morandi |first4=Bill |journal=Science |volume=356 |issue=6342 |pages=1059–1063 |pmid=28596362 |bibcode=2017Sci...356.1059L |s2cid=206657928 }} It can also be prepared by reduction of diphenyl sulfone.{{cite journal | url=https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cber.18930260393 | doi=10.1002/cber.18930260393 | title=Ueber Umwandlung des Diphenylsulfons in Diphenylsulfid und Diphenylselenid | date=1893 | last1=Krafft | first1=F. | last2=Vorster | first2=W. | journal=Berichte der Deutschen Chemischen Gesellschaft | volume=26 | issue=3 | pages=2813–2822 }}
Diphenyl sulfide is a product of the photodegradation of the fungicide edifenphos.{{cite journal |doi=10.1080/00021369.1977.10862468 |title=Photodecomposition of O -Ethyl S , S -Diphenyl Phosphorodithiolate (Edifenphos) |date=1977 |last1=Murai |first1=Toshinobu |journal=Agricultural and Biological Chemistry |volume=41 |pages=71–77 }}
Diphenyl sulfide is a precursor to triarylsulfonium salts, which are used as photoinitiators. The compound can be oxidized to the sulfoxide with hydrogen peroxide.{{cite journal |doi=10.1016/s0040-4020(01)00068-0 |title=Oxidation of Sulfides to Sulfoxides and Sulfones with 30% Hydrogen Peroxide under Organic Solvent- and Halogen-Free Conditions |date=2001 |last1=Sato |first1=Kazuhiko |last2=Hyodo |first2=Mamoru |last3=Aoki |first3=Masao |last4=Zheng |first4=Xiao-Qi |last5=Noyori |first5=Ryoji |journal=Tetrahedron |volume=57 |issue=13 |pages=2469–2476 }}