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Revision as of 13:30, 17 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit Latest revision as of 21:04, 10 April 2024 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,495 edits →Preparation and structure: ref repair 
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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 402002389 | verifiedrevid = 414430474
⚫ | Name = Diphenyl disulfide
| ImageFile = Diphenyl disulfide.png | Name = Diphenyl disulfide
⚫ | ImageFile = Diphenyl-disulfide-2D-skeletal.svg
<!-- | ImageSize = 200px --> | ImageSize = 200px
| ImageName = Skeletal formula of diphenyl disulfide
| PIN = 1,1′-Disulfanediyldibenzene
| ImageFile1 = Diphenyl-disulfide-from-xtal-3D-balls.png
| OtherNames = Disulfanyldibenzene<br />Diphenyl disulfide<br />Phenyl disulfide<br />1,2-Diphenyldisulfane (not recommended)
<!-- | ImageSize1 = 230px -->
⚫ |Section1={{Chembox Identifiers
| ImageName1 = Ball-and-stick model of diphenyl disulfide
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
| PIN = Disulfanyldibenzene
⚫ | CASNo = 882-33-7
| IUPACName = Diphenyl disulfide
| ChEBI = 174102
| OtherNames = Phenyl disulfide
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | Section1 = {{Chembox Identifiers
⚫ | SMILES = c1ccc(cc1)SSc2ccccc2
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12861 | ChemSpiderID = 12861
| PubChem = 13436 | PubChem = 13436
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 462861
| EC_number = 212-926-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7P54H519IJ
⚫ | RTECS = SS6825000
| InChI = 1/C12H10S2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H | InChI = 1/C12H10S2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H
| InChIKey = GUUVPOWQJOLRAS-UHFFFAOYAY | InChIKey = GUUVPOWQJOLRAS-UHFFFAOYAY
⚫ | ChEMBL = 462861
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H10S2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H | StdInChI = 1S/C12H10S2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GUUVPOWQJOLRAS-UHFFFAOYSA-N | StdInChIKey = GUUVPOWQJOLRAS-UHFFFAOYSA-N
⚫ | SMILES = c1ccc(cc1)SSc2ccccc2
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 882-33-7
⚫ | RTECS = SS6825000
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=12|H=10|S=2
| Formula = C<sub>12</sub>H<sub>10</sub>S<sub>2</sub>
⚫ | Appearance = Colorless crystals
| MolarMass = 218.36 g/mol
| Density =
⚫ | Appearance = Colourless crystals
⚫ | Solubility = Insoluble
| Density = ? g/cm<sup>3</sup>
⚫ | Solvent = other solvents
⚫ | Solubility = Insoluble
⚫ | SolubleOther = Soluble in ], ], ], and ]
⚫ | Solvent = other solvents
| MeltingPtC = 61 to 62
⚫ | SolubleOther = ],<br />],<br />],<br />]
| MeltingPt = 61–62 °C | BoilingPt =
| BoilingPt =
}} }}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| CrystalStruct = | CrystalStruct =
| Dipole = 0 ] | Dipole = 0 ]
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = Flammable | MainHazards = Flammable
| FlashPt = | FlashPt =
| GHS_ref=<ref>{{cite web |title=Diphenyl disulfide |url=https://pubchem.ncbi.nlm.nih.gov/compound/13436#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=13 December 2021 |language=en}}</ref>
| RPhrases = 36/37/38
| GHSPictograms = {{GHS07}}
| SPhrases = 26
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|273|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|391|403+233|405|501}}
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| OtherCpds = ],<br />],<br />] | OtherCompounds = ],<br />],<br />]
}} }}
}} }}


'''Diphenyl disulfide''' is the ] with the formula <sub>2</sub>. This colorless crystalline material is often abbreviated Ph<sub>2</sub>S<sub>2</sub>. It is one of the most popular organic ]s used in ]. Minor contamination by ] is responsible for the disagreeable odour associated with this compound. '''Diphenyl disulfide''' is the ] with the formula (C<sub>6</sub>H<sub>5</sub>S)<sub>2</sub>. This colorless crystalline material is often abbreviated Ph<sub>2</sub>S<sub>2</sub>. It is one of the more commonly encountered organic ]s in ]. Minor contamination by ] is responsible for the disagreeable odour associated with this compound.


==Preparation and structure== ==Preparation and structure==
Ph<sub>2</sub>S<sub>2</sub> is usually prepared by the oxidation of thiophenol: Diphenyl disulfide is usually prepared by the oxidation of ]:
: 2 PhSH + ] &rarr; Ph<sub>2</sub>S<sub>2</sub> + 2 HI : 2 PhSH + ] → Ph<sub>2</sub>S<sub>2</sub> + 2 HI
] can also be used as the oxidant.<ref>{{OrgSynth | author = Ravikumar,K. S.; Kesavan, V.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. | title = Mild and Selective Oxidation of Sulfur Compounds in Trifluoroethanol: Diphenyl Disulfide and Methyl Phenyl Sulfoxide | volume = 80 | pages = 184 | year = 2003 | prep = v80p0184}}</ref> Ph<sub>2</sub>S<sub>2</sub> is rarely prepared in the laboratory because it is inexpensive, and the precursor has a disagreeable odour. ] can also be used as the oxidant.<ref>{{OrgSynth | author = Ravikumar,K. S. | author2 = Kesavan, V. | author3 = Crousse, B. | author4 = Bonnet-Delpon, D. | author5 = Bégué, J.-P. | title = Mild and Selective Oxidation of Sulfur Compounds in Trifluoroethanol: Diphenyl Disulfide and Methyl Phenyl Sulfoxide | volume = 80 | pages = 184 | year = 2003 | doi = 10.15227/orgsyn.080.0184}}</ref> Ph<sub>2</sub>S<sub>2</sub> is rarely prepared in the laboratory because it is inexpensive, and the precursor has a disagreeable odour.


Like most organic disulfides, the C<sub>2</sub>S<sub>2</sub> core of Ph<sub>2</sub>S<sub>2</sub> is non-planar with a dihedral angle approaching 85°. Like most organic disulfides, the C–S–S–C core of Ph<sub>2</sub>S<sub>2</sub> is non-planar with a dihedral angle approaching 85°.<ref>{{cite journal|doi=10.1107/S0567740869005188 |title=The Crystal Structure of Diphenyl Disulphide |date=1969 |last1=Lee |first1=J. D. |last2=Bryant |first2=M. W. R. |journal=Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry |volume=25 |issue=10 |pages=2094–2101 |bibcode=1969AcCrB..25.2094L }}</ref>
].]]


==Reactions== ==Reactions==
Ph<sub>2</sub>S<sub>2</sub> is mainly used in organic synthesis as a source of the PhS substituent.<ref>Byers, J. H. "Diphenyl Disulfide" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.</ref> A typical reaction entails the formation of PhS-substituted carbonyl compounds via the ]: Ph<sub>2</sub>S<sub>2</sub> is mainly used in organic synthesis as a source of the PhS substituent.<ref>{{cite book|author=Byers, J. H.|chapter=Diphenyl Disulfide|title=Encyclopedia of Reagents for Organic Synthesis'' (Ed: L. Paquette)|year=2004|editor=J. Wiley & Sons|location=New York|doi=10.1002/047084289X|hdl=10261/236866 |isbn=9780471936237 }}.</ref> A typical reaction entails the formation of PhS-substituted carbonyl compounds via the ]:
:RC(O)CHLiR’ + Ph<sub>2</sub>S<sub>2</sub> &rarr; RC(O)CH(SPh)R’ + LiSPh :RC(O)CHLiR' + Ph<sub>2</sub>S<sub>2</sub> → RC(O)CH(SPh)R' + LiSPh


===Reduction=== ===Reduction===
Ph<sub>2</sub>S<sub>2</sub> undergoes reduction, a reaction characteristic of disulfides: Ph<sub>2</sub>S<sub>2</sub> undergoes reduction, a reaction characteristic of disulfides:
:Ph<sub>2</sub>S<sub>2</sub> + 2 M &rarr; 2 MSPh (M = Li, Na, K) :Ph<sub>2</sub>S<sub>2</sub> + 2 M → 2 MSPh (M = Li, Na, K)
Hydride reagents such as ] and ] can also be used as reductants. Hydride reagents such as ] and ] can also be used as reductants.
The salts PhSM are sources of the potent ] PhS<sup>-</sup>. Most ]s, RX (X = halide) convert it to the ]s with the general formula RSPh. Analogously, protonation of MSPh gives thiophenol: The salts PhSM are sources of the potent ] PhS<sup>−</sup>. Most ]s, RX (X = halide) convert it to the ]s with the general formula RSPh. Analogously, protonation of MSPh gives thiophenol:
:PhSM + HCl &rarr; HSPh + MCl :PhSM + HCl → HSPh + MCl


===Chlorination=== ===Halogenation===
Ph<sub>2</sub>S<sub>2</sub> reacts with ] to give ] PhSCl (]). This species is somewhat difficult to isolate, so it is usually generated in situ. Ph<sub>2</sub>S<sub>2</sub> reacts with ] to give ] PhSCl (]). This species is usually generated and used '']''. With ], Ph<sub>2</sub>S<sub>2</sub> reacts to give ].<ref>{{Cite journal |last1=Sergeeva |first1=Tatiana A. |last2=Dolbier |first2=William R. |date=2004-07-01 |title=A New Synthesis of Pentafluorosulfanylbenzene |url=https://pubs.acs.org/doi/10.1021/ol0491991 |journal=Organic Letters |language=en |volume=6 |issue=14 |pages=2417–2419 |doi=10.1021/ol0491991 |pmid=15228293 |issn=1523-7060}}</ref>


===Catalyst for photoisomerisation of alkenes=== ===Catalyst for photoisomerization of alkenes===
Ph<sub>2</sub>S<sub>2</sub>catalyzes the cis-trans isomerization of alkenes under UV-irradiation.<ref>{{OrgSynth | author = Thalmann, A. Oertle, K.; Gerlach, H. | title = Ricinelaidic Acid Lactone | collvol = 7 | collvolpages = 470 | year = 1990 | prep = cv7p0470}}</ref> Ph<sub>2</sub>S<sub>2</sub> catalyzes the ] of ]s under UV-irradiation.<ref>{{OrgSynth | author = Thalmann, A. Oertle, K. | author2 = Gerlach, H. | title = Ricinelaidic Acid Lactone | collvol = 7 | collvolpages = 470 | year = 1990 | prep = cv7p0470}}</ref>


===Oxidation=== ===Oxidation===
Oxidation of Ph<sub>2</sub>S<sub>2</sub> with ] (Pb(OAc)<sub>4</sub>) in ] affords the sulfinite ester PhS(O)OMe.<ref>{{OrgSynth | author = Field, L.; Locke, J. M. | title = Methyl Benzenesulfinate | collvol = 5 | collvolpages = 723 | year = 1973 | prep = cv5p0723}}</ref> Oxidation of Ph<sub>2</sub>S<sub>2</sub> with ] (Pb(OAc)<sub>4</sub>) in ] affords the sulfinite ester PhS(O)OMe.<ref>{{OrgSynth | author = Field, L. | author2 = Locke, J. M. | title = Methyl Benzenesulfinate | collvol = 5 | collvolpages = 723 | year = 1973 | prep = cv5p0723}}</ref>


==References== ==References==
{{Reflist}}
<references/>


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