Diphenyl sulfide

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.

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
Odor	Unpleasant
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

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.^[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]