Diphenyl sulfide

Organic compound

Diphenyl sulfide

Names
IUPAC name

Phenylsulfanylbenzene

Identifiers

CAS Number

* 139-66-2

3D model (JSmol)

* Interactive image

Abbreviations  | Ph2S

Beilstein Reference

| 1907932
ChEBI |

* CHEBI:38959

ChEMBL |

* ChEMBL219876

ChemSpider |

* 8436

ECHA InfoCard | 100.004.884
EC Number |

* 205-371-4

UNII |

* B5P3Y93MNR

CompTox Dashboard (EPA)

* DTXSID8044383

InChI

* InChI=1S/C12H10S/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H

Key: LTYMSROWYAPPGB-UHFFFAOYSA-N

SMILES

* C1=CC=C(C=C1)SC2=CC=CC=C2

Properties

Chemical formula

| (C6H5)2S
Molar mass | 186.27 g·mol−1
Appearance  | Colorless liquid
Density | 1.113 g/cm3 (20 °C)[1]
Vapor: 6.42 (air = 1.0)
Melting point | −25.9 °C (−14.6 °F; 247.2 K)
Boiling point | 296 °C (565 °F; 569 K)

Solubility in water

| insoluble
Solubility | Soluble in diethyl ether, benzene, carbon disulfide.
Vapor pressure | 0.01 hPa at 25 °C[2]

Refractive index (nD)

| 1.6327
Viscosity |

* 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

Structure

Molecular shape

| Bent on the sulfur atom
Hazards
GHS labelling:

Pictograms

Signal word

| Warning

Hazard statements

| H302, H315, H319, H410

Precautionary statements

| P264, P270, P273, P280, P301+P312, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P362+P364, P391, P501
Flash point | 113 °C (235 °F)
Lethal dose or concentration (LD, LC):

LD50 (median dose)

* 300 to 2000 mg/kg (oral, female rat)
* 5000 mg/kg (dermal, female rat)
* 11300 μL/kg (dermal, rabbit)[3]
* 490 μL/kg (oral, rat)
* 545 mg/kg (oral, rat)
* 12600 mg/kg (dermal, rabbit)[2]

Related compounds

Related compounds

* Diphenyl ether
* Diphenyl selenide
* Diphenyl telluride
* Diphenyl disulfide
* Thiophenol
* Diphenyl sulfone

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

Infobox references

Chemical compound

Diphenyl sulfide is an organosulfur compound with the chemical formula (C6H5)2S, often abbreviated as 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

[edit]

Many methods exist for the preparation of diphenyl sulfide. It arises by a Friedel-Crafts-like reaction of sulfur monochloride and benzene.[4] Diphenyl sulfide and its analogues can also be produced by coupling reactions using metal catalysts.[5] It can also be prepared by reduction of diphenyl sulfone.[6]

Diphenyl sulfide is a product of the photodegradation of the fungicide edifenphos.[7]

Diphenyl sulfide is a precursor to triarylsulfonium salts, which are used as photoinitiators. The compound can be oxidized to the sulfoxide with hydrogen peroxide.[8]

## References

[edit]

1. ^ "3". CRC Handbook of Chemistry and Physics (90 ed.). 2010. p. 220.
2. ^ a b "GESTIS-Stoffdatenbank".
3. ^ "Diphenyl sulfide".
4. ^ Hartman, W. W.; Smith, L. A.; Dickey, J. B. (1934). "Diphenyl Sulfide". Organic Syntheses. 14: 36. doi:10.15227/orgsyn.014.0036.
5. ^ Lian, Zhong; Bhawal, Benjamin N.; Yu, Peng; Morandi, Bill (2017). "Palladium-catalyzed carbon-sulfur or carbon-phosphorus bond metathesis by reversible arylation". Science. 356 (6342): 1059–1063\. Bibcode:2017Sci...356.1059L. doi:10.1126/science.aam9041. PMID 28596362. S2CID 206657928.
6. ^ Krafft, F.; Vorster, W. (1893). "Ueber Umwandlung des Diphenylsulfons in Diphenylsulfid und Diphenylselenid". Berichte der Deutschen Chemischen Gesellschaft. 26 (3): 2813–2822\. doi:10.1002/cber.18930260393.
7. ^ Murai, Toshinobu (1977). "Photodecomposition of O -Ethyl S , S -Diphenyl Phosphorodithiolate (Edifenphos)". Agricultural and Biological Chemistry. 41: 71–77\. doi:10.1080/00021369.1977.10862468.
8. ^ Sato, Kazuhiko; Hyodo, Mamoru; Aoki, Masao; Zheng, Xiao-Qi; Noyori, Ryoji (2001). "Oxidation of Sulfides to Sulfoxides and Sulfones with 30% Hydrogen Peroxide under Organic Solvent- and Halogen-Free Conditions". Tetrahedron. 57 (13): 2469–2476\. doi:10.1016/s0040-4020(01)00068-0.

*[EPA]: U.S. Environmental Protection Agency
*[H302]: H302: Harmful if swallowed
*[H315]: H315: Causes skin irritation
*[H319]: H319: Causes serious eye irritation
*[H410]: H410: Very toxic to aquatic life with long lasting effects
*[P264]: P264: Wash ... thoroughly after handling.
*[P270]: P270: Do not eat, drink or smoke when using this product.
*[P273]: P273: Avoid release to the environment.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P301+P312]: P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
*[P301+P317]: P301+P317: IF SWALLOWED: IF SWALLOWED: Get medical help.
*[P302+P352]: P302+P352: IF ON SKIN: Wash with soap and water.
*[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.
*[P321]: P321: Specific treatment (see ... on this label).
*[P330]: P330: Rinse mouth.
*[P332+P317]: P332+P317: If skin irritation occurs: Get medical help.
*[P362+P364]: P362+P364: Take off contaminated clothing and wash it before reuse.
*[P391]: P391: Collect spillage.
*[P501]: P501: Dispose of contents/container to ...