Diphenyl disulfide

Names
Preferred IUPAC name

1,1′-Disulfanediyldibenzene

Other names

Disulfanyldibenzene
Diphenyl disulfide
Phenyl disulfide
1,2-Diphenyldisulfane (not recommended)

Identifiers

CAS Number

* 882-33-7 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:174102

ChEMBL |

* ChEMBL462861 Y

ChemSpider |

* 12861 Y

ECHA InfoCard | 100.011.752
EC Number |

* 212-926-4

PubChem CID

* 13436

RTECS number |

* SS6825000

UNII |

* 7P54H519IJ Y

CompTox Dashboard (EPA)

* DTXSID6022131

InChI

* InChI=1S/C12H10S2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H Y

Key: GUUVPOWQJOLRAS-UHFFFAOYSA-N Y

* InChI=1/C12H10S2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H

Key: GUUVPOWQJOLRAS-UHFFFAOYAY

SMILES

* c1ccc(cc1)SSc2ccccc2

Properties

Chemical formula

| C12H10S2
Molar mass | 218.33 g·mol−1
Appearance  | Colorless crystals
Melting point | 61 to 62 °C (142 to 144 °F; 334 to 335 K)

Solubility in water

| Insoluble
Solubility in other solvents  | Soluble in diethyl ether, benzene, carbon disulfide, and THF
Structure

Dipole moment

| 0 D
Hazards
Occupational safety and health (OHS/OSH):

Main hazards

| Flammable
GHS labelling:[1]

Pictograms

Signal word

| Warning

Hazard statements

| H315, H319, H335

Precautionary statements

| P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
Related compounds

Related compounds

| Thiophenol,
Dimethyl disulfide,
Diphenyl diselenide

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)

Infobox references

Chemical compound

Diphenyl disulfide is the chemical compound with the formula (C6H5S)2. This colorless crystalline material is often abbreviated Ph2S2. It is one of the more commonly encountered organic disulfides in organic synthesis. Minor contamination by thiophenol is responsible for the disagreeable odour associated with this compound.

## Preparation and structure

[edit]

Diphenyl disulfide is usually prepared by the oxidation of thiophenol:

2 PhSH + I2 → Ph2S2 \+ 2 HI

Hydrogen peroxide can also be used as the oxidant.[2] Ph2S2 is rarely prepared in the laboratory because it is inexpensive, and the precursor has a disagreeable odour.

Like most organic disulfides, the C–S–S–C core of Ph2S2 is non-planar with a dihedral angle approaching 85°.[3]

Ball-and-stick model of diphenyl disulfide. The S-S bond distance is 2.03 Å.

## Reactions

[edit]

Ph2S2 is mainly used in organic synthesis as a source of the PhS substituent.[4] A typical reaction entails the formation of PhS-substituted carbonyl compounds via the enolate:

RC(O)CHLiR' + Ph2S2 → RC(O)CH(SPh)R' + LiSPh

### Reduction

[edit]

Ph2S2 undergoes reduction, a reaction characteristic of disulfides:

Ph2S2 \+ 2 M → 2 MSPh (M = Li, Na, K)

Hydride reagents such as sodium borohydride and super hydride can also be used as reductants. The salts PhSM are sources of the potent nucleophile PhS−. Most alkyl halides, RX (X = halide) convert it to the thioethers with the general formula RSPh. Analogously, protonation of MSPh gives thiophenol:

PhSM + HCl → HSPh + MCl

### Halogenation

[edit]

Ph2S2 reacts with chlorine to give phenylsulfenyl chloride PhSCl (Zincke disulfide cleavage). This species is usually generated and used in situ. With xenon difluoride, Ph2S2 reacts to give phenylsulfur pentafluoride.[5]

### Catalyst for photoisomerization of alkenes

[edit]

Ph2S2 catalyzes the cis-trans isomerization of alkenes under UV-irradiation.[6]

### Oxidation

[edit]

Oxidation of Ph2S2 with lead(IV) acetate (Pb(OAc)4) in methanol affords the sulfinite ester PhS(O)OMe.[7]

## References

[edit]

1. ^ "Diphenyl disulfide". pubchem.ncbi.nlm.nih.gov. Retrieved 13 December 2021.
2. ^ Ravikumar,K. S.; Kesavan, V.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. (2003). "Mild and Selective Oxidation of Sulfur Compounds in Trifluoroethanol: Diphenyl Disulfide and Methyl Phenyl Sulfoxide". Organic Syntheses. 80: 184. doi:10.15227/orgsyn.080.0184.
3. ^ Lee, J. D.; Bryant, M. W. R. (1969). "The Crystal Structure of Diphenyl Disulphide". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 25 (10): 2094–2101\. Bibcode:1969AcCrB..25.2094L. doi:10.1107/S0567740869005188.
4. ^ Byers, J. H. (2004). "Diphenyl Disulfide". In L. Paquette) (ed.). Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons. doi:10.1002/047084289X. hdl:10261/236866. ISBN 9780471936237..
5. ^ Sergeeva, Tatiana A.; Dolbier, William R. (2004-07-01). "A New Synthesis of Pentafluorosulfanylbenzene". Organic Letters. 6 (14): 2417–2419\. doi:10.1021/ol0491991. ISSN 1523-7060. PMID 15228293.
6. ^ Thalmann, A.; Oertle, K.; Gerlach, H. (1990). "Ricinelaidic Acid Lactone". Organic Syntheses; Collected Volumes, vol. 7, p. 470.
7. ^ Field, L.; Locke, J. M. (1973). "Methyl Benzenesulfinate". Organic Syntheses; Collected Volumes, vol. 5, p. 723.

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H315]: H315: Causes skin irritation
*[H319]: H319: Causes serious eye irritation
*[H335]: H335: May cause respiratory irritation
*[P261]: P261: Avoid breathing dust/fume/gas/mist/vapours/spray.
*[P264]: P264: Wash ... thoroughly after handling.
*[P271]: P271: Use only outdoors or in a well-ventilated area.
*[P273]: P273: Avoid release to the environment.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P302+P352]: P302+P352: IF ON SKIN: Wash with soap and water.
*[P304+P340]: P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
*[P305+P351+P338]: P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
*[P312]: P312: Call a POISON CENTER or doctor/physician if you feel unwell.
*[P321]: P321: Specific treatment (see ... on this label).
*[P332+P313]: P332+P313: If skin irritation occurs: Get medical advice/attention.
*[P337+P313]: P337+P313: If eye irritation persists: Get medical advice/attention.
*[P362]: P362: Take off contaminated clothing.
*[P391]: P391: Collect spillage.
*[P403+P233]: P403+P233: Store in a well ventilated place. Keep container tightly closed.
*[P405]: P405: Store locked up.
*[P501]: P501: Dispose of contents/container to ...