Chemistry:Diphenyl sulfide

Short description: 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
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	(C 6H 5) 2S
Molar mass	186.27 g·mol−1
Appearance	Colorless liquid
Density	1.113 g/cm3 (20 °C) 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
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 pictograms
GHS Signal word	Warning
GHS hazard statements	HH302Category:GHS errors, HH315Category:GHS errors, HH319Category:GHS errors, HH410Category:GHS errors
GHS precautionary statements	PP264Category:GHS errors, PP270Category:GHS errors, PP273Category:GHS errors, PP280Category:GHS errors, PP301+P312Category:GHS errors, PP301+P317Category:GHS errors, PP302+P352Category:GHS errors, PP305+P351+P338Category:GHS errors, PP321Category:GHS errors, PP330Category:GHS errors, PP332+P317Category:GHS errors, PP362+P364Category:GHS errors, PP391Category:GHS errors, PP501Category:GHS errors
Flash point	113 °C (235 °F)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	300 to 2000 mg/kg (oral, female rat)</ref> 5000 mg/kg (dermal, female rat) 11300 μL/kg (dermal, rabbit) 490 μL/kg (oral, rat)</ref> 545 mg/kg (oral, rat) 12600 mg/kg (dermal, rabbit)
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

Diphenyl sulfide is an organosulfur compound with the chemical formula (C
6H
5)
2S, often abbreviated as Ph
2S, 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.Diphenyl sulfide and its analogues can also be produced by coupling reactions using metal catalysts. It can also be prepared by reduction of diphenyl sulfone.

Diphenyl sulfide is a product of the photodegradation of the fungicide edifenphos.

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