19813-97-9

Basic information

• Product Name: 2-Biphenylyl disulfide
• CAS NO: 19813-97-9
• Molecular Formula: C₂₄H₁₈S₂
• Molecular Weight: 370.539
• Mol File: 19813-97-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 521.5°Cat760mmHg
• Flash Point: 298.4°C
• Density: 1.24g/cm³
• CAS DataBase Reference: 2-Biphenylyl disulfide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Biphenylyl disulfide(19813-97-9)
• EPA Substance Registry System: 2-Biphenylyl disulfide(19813-97-9)

Safety Data

• Hazardous Substances Data: 19813-97-9(Hazardous Substances Data)

Upstream product

• 2688-96-2 2-phenylbenzenethiol 
• 99847-58-2 [1,1’-biphenyl]-2-yl thiocyanate 
• 90-43-7 2-Phenylphenol 
• 37692-10-7 2-Phenylbenzensulfenanilid 
• 110228-48-3 4'-methoxybiphenyl-2-sulphenanilide 
• 110228-47-2 4'-nitrobiphenyl-2-sulphenanilide 
• 110228-53-0 4'-(biphenyl-2-ylthio)biphenyl-2-sulphenanilide 
• 40182-14-7 [1,1′-biphenyl]-2-sulfonyl azide 
• 318-13-8 [1,1'-biphenyl]-2-diazonium tetrafluoroborate 
• 37692-16-3 2-phenylbenzenesulphenyl chloride 
• 2688-90-6 2-phenylbenzenesulfonyl chloride 
• 2113-51-1 2-iodobiphenyl 
• 90-41-5 2-phenylaniline 

Downstream Products

• 132-65-0 dibenzothiophene 

Relevant articles and documents

Insertion of [1.1.1]propellane into aromatic disulfides

Herein we present the synthesis of symmetrically and unsymmetrically substituted 1,3-bissulfanylbicyclo[1.1.1]pentanes from disulfides and [1.1.1]propellane. Bicyclo[1.1.1]pentanes (BCPs) recently gained interest as rigid linkers and as bioisosters of parasubstituted benzene and alkyne moieties. The most promising precursor for BCPs is [1.1.1]propellane (1). The available methods to synthesize BCPs are quite limited and many groups contribute to the development of novel methods. The insertion of 1 into disulfide bonds is known, but has never been thoroughly investigated. In this study, we show that an UV initiated radical reaction can be used to synthesize symmetrically and unsymmetrically substituted BCP sulfides by reaction of [1.1.1]propellane (1) with disulfides. Depending on the ratio of 1 to the disulfide, only the BCP product (with up to 98% yield) or a mixture of BCP and [2]staffane can be obtained. The reaction tolerates functional groups such as halogens, alkyl and methoxy groups. The separation of the corresponding BCP and [2]staffane products is challenging but possible by column chromatography and preparative TLC in most cases. Single crystal X-ray diffraction analysis confirms the rod-like structure of the [2]staffanes that is often required in material applications.

Palladium(II)-Catalyzed Synthesis of Dibenzothiophenes from 2-Biphenylyl Disulfides by C?H Functionalization

The palladium-catalyzed oxidative preparation of dibenzothiophene derivatives from 2-biphenylyl disulfides by C?H functionalization is described herein. This procedure shows a high tolerance toward various functional groups and does not require the further addition of a metal oxidant, a base, or a ligand. Also, the present method was applied to the facile preparation of dibenzoselenophene.

THERMAL REACTIVITY OF 4'SUBSTITUTED- AND 4'-SUBSTITUTED-2-PHENYL-BENZENESUPHENANILIDES

The thermal decomposition of 4'-nitro, 4'-H, and 4'-methoxy-benzenesulphenanilides in benzene and/or furan, and of 4'-substituted-2-phenylbenzenesulphenanilides ( 1d-1f ) in benzene, was found to proceed by two distinct pathways: ( i ) nucleophilic displacement by furan and/or another sulphenanilide unit and ( ii ) homolytic S-N bond fission to give sulphenyl and anilino radicals.An increase in the electron-withdrawning capability of the 4'-substituted favours the ionic pathway, whwreas the radical pathway is favoured by an increase in the reaction temperature.