3379-36-0

Basic information

• Product Name: 1,2-Bis(phenylthio)benzene
• Synonyms: 1,2-Bis(phenylthio)benzene;2-(phenylthio)diphenyl sulfide
• CAS NO: 3379-36-0
• Molecular Formula: C₁₈H₁₄S₂
• Molecular Weight: 294.4338
• Mol File: 3379-36-0.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 422.2°Cat760mmHg
• Flash Point: 210.7°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 6.03E-07mmHg at 25°C
• Refractive Index: 1.702
• CAS DataBase Reference: 1,2-Bis(phenylthio)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Bis(phenylthio)benzene(3379-36-0)
• EPA Substance Registry System: 1,2-Bis(phenylthio)benzene(3379-36-0)

Safety Data

• Hazardous Substances Data: 3379-36-0(Hazardous Substances Data)

Usage

Physical state

Colorless solid

Solubility

Insoluble in water

Primary uses

a. Intermediate in the production of dyes
b. Intermediate in the production of pharmaceuticals
c. Intermediate in the production of other organic compounds

Additional uses

a. Crosslinking agent in polymer production
b. Reagent in organic synthesis

Hazards

a. Harmful if swallowed
b. Causes skin and eye irritation upon contact
c. Flammable

Safety precautions

Handle with caution due to flammability and potential for skin and eye irritation.

InChI:InChI=1/C18H14S2/c1-3-9-15(10-4-1)19-17-13-7-8-14-18(17)20-16-11-5-2-6-12-16/h1-14H

Upstream product

• 1192-40-1 copper(I) thiophenolate 
• 95-50-1 1,2-dichloro-benzene 
• 583-53-9 2,3-dibromobenzene 
• 615-41-8 2-iodochlorobenzene 
• 930-69-8 sodium thiophenolate 
• 1956-97-4 2-chlorobenzenediazonium tetrafluoroborate 
• 7169-58-6 1-(2-iodophenyl)diazonium tetrafluoroborate 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 107046-32-2 C₁₂H₉ClN₂S 
• 85609-04-7 1,2-bis(ethylthio)benzene 
• 118-92-3 anthranilic acid 
• 882-33-7 diphenyldisulfane 
• 108-98-5 thiophenol 
• 1488-42-2 Diphenyliodonium-2-carboxylate 

Downstream Products

• 102059-02-9 1,2-bis(phenylsulphonyl)benzene 
• 1016-05-3 dibenzothiophene sulfone 
• 127-63-9 diphenyl sulphone 
• 64939-42-0 1-(phenylsulphonyl)-2-(phenylthio)benzene 
• 71499-03-1 dibromo[1,2-bis(phenylthio)benzene]platinum(II) 
• 75674-77-0 [Os(o-C₆H₄(SPh)2)Cl₄] 
• 71499-02-0 dichloro[1,2-bis(phenylthio)benzene]platinum(II) 
• 71499-00-8 dibromo[1,2-bis(phenylthio)benzene]palladium(II) 
• 71499-04-2 diiodo[1,2-bis(phenylthio)benzene]platinum(II) 
• 71498-99-2 dichloro[1,2-bis(phenylthio)benzene]palladium(II) 

Relevant articles and documents

Insertion of Benzyne and Substituted Benzynes into the S-S Bond of Diphenyl and Di-p-tolyl Disulfides Yielding the Corresponding o-Bis(arylthio)benzenes

Benzyne and substituted benzynes undergo insertion into the S-S bond of diphenyl and di-p-tolyl disulfides to afford the corresponding o-bis(arylthio)benzenes in low but reproducible yields.

Transformations of diphenyl sulfide and diphenylamine on aluminum chloride

Thianthrene has been synthesized by reacting diphenyl sulfide with AlCl3 in heptane at 98°C for 8 h at a diphenyl sulfide: AlCl3 molar ratio of 2: 1; the thianthrene yield is 58%. The reaction mechanism proposed previously has been confirmed by quantum-chemical calculations; the reaction is characterized by a low negative value of Gibbs free energy, a low heat of reaction, and a high activation energy of the first step. Diphenyl ether and diphenylamine do not enter the test reaction because of low nucleophilicity of the heteroatoms; diphenylamine dimerizes under the reaction conditions to form N,N′-diphenylbenzidine.

Generation of Aryl Radicals from Aryl Halides: Rongalite-Promoted Transition-Metal-Free Arylation

A new and practical method for the generation of aryl radicals from aryl halides is reported. Rongalite as a novel precursor of super electron donors was used to initiate a series of electron-catalyzed reactions under mild conditions. These transition-metal-free radical chain reactions enable the efficient formation of C-C, C-S, and C-P bonds through homolytic aromatic substitution or SRN1 reactions. Moreover, the synthesis of antipsychotic drug Quetiapine was performed on gram scale through the described method. This protocol demonstrated its potential as a promising arylation method in organic synthesis.