3459-94-7

Basic information

• Product Name: Benzene, 1,4-bis(phenylthio)-
• Synonyms: 1,4-Bis(phenylsulfanyl)benzene
• CAS NO: 3459-94-7
• Molecular Formula: C₁₈H₁₄S₂
• Molecular Weight: 294.441
• Mol File: 3459-94-7.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 467.5 °C at 760 mmHg
• Flash Point: 245.6 °C
• Density: 1.23 g/cm³
• CAS DataBase Reference: Benzene, 1,4-bis(phenylthio)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,4-bis(phenylthio)-(3459-94-7)
• EPA Substance Registry System: Benzene, 1,4-bis(phenylthio)-(3459-94-7)

Safety Data

• Hazardous Substances Data: 3459-94-7(Hazardous Substances Data)

Usage

General Description

Benzene, 1,4-bis(phenylthio)-, also known as biphenyl-4-thiol, is a chemical compound with the molecular formula C24H18S2. It is a yellowish-white solid and is often used as a building block in the synthesis of various polymers and organic compounds. It is also used as a cross-linking agent in the production of rubbers and plastics. Additionally, 1,4-bis(phenylthio)-benzene has been studied for its potential use as a photoconductor material and as a component in organic electronic devices. However, it is important to handle this compound with caution, as it is considered to be harmful if swallowed or inhaled, and may cause skin and eye irritation upon contact.

Upstream product

• 106-46-7 para-dichlorobenzene 
• 1192-40-1 copper(I) thiophenolate 
• 106-37-6 1.4-dibromobenzene 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 930-69-8 sodium thiophenolate 
• 624-38-4 para-diiodobenzene 
• 882-33-7 diphenyldisulfane 
• 589-87-7 1,4-bromoiodobenzene 
• 108-98-5 thiophenol 
• 106-39-8 bromochlorobenzene 
• 98-80-6 phenylboronic acid 
• 637-87-6 1-Chloro-4-iodobenzene 
• 4612-26-4 1,4-Phenyldiboronic acid 
• 873-55-2 sodium benzenesulfonate 

Downstream Products

• 241-34-9 benzo[1, 2-b: 4, 5-b']bis[b]benzothiophene 
• 59090-58-3 1-(phenylsulfinyl)-4-(phenylsulfinyl)benzene 
• 134983-66-7 C₃₀H₂₂O₈S₄ 
• 134983-65-6 1,4-bis((4-bromophenyl)sulfonyl)benzene 
• 3379-65-5 1,4-di(p-phenylthio)phenylthiobenzene 
• 99901-62-9 C₁₈H₁₄S₂O 
• 41518-53-0 1,4-bis((4-bromophenyl)thio)benzene 
• 71449-78-0 4-thiophenoxyphenyl(diphenyl)sulfonium hexafluoroantimonate 
• 27375-45-7 1,4-bis-benzenesulfonyl-benzene 

Relevant articles and documents

Environmentally Friendly and Recyclable CuCl 2-Mediated C-S Bond Coupling Strategy Using DMEDA as Ligand, Base, and Solvent

Simple reaction conditions and recyclable reagents are crucial for environmentally friendly industrial applications. An environment-friendly, recyclable and economic strategy was developed to synthesize diaryl chalcogenides by the CuCl2-catalyzed C S bondformation reaction via iodobenzenes and benzenethiols/1,2-diphenyldisulfanes using N,N'-dimethylethane-1,2-diamine (DMEDA) as ligand, base, and solvent. For these reactions, especially the reactions of diiodobenzenes and aminobenzenethiols/disulfanediyldianilines, a range of substrates are compatible and give the corresponding products in good to excellent yields. Both of the reagents in the catalytic system (CuCl2/DMEDA) are inexpensive, conveniently separable, and recyclable for more than five cycles.

Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C?S/C?N Couplings

Ni-catalyzed C?S cross-coupling reactions have received less attention compared with other C-heteroatom couplings. Most reported examples comprise the thioetherification of most reactive aryl iodides with aromatic thiols. The use of C?O electrophiles in this context is almost uncharted. Here, we describe that preformed Ni(II) precatalysts of the type NiCl(allyl)(PMe2Ar’) (Ar’=terphenyl group) efficiently couple a wide range of (hetero)aryl halides, including challenging aryl chlorides, with a variety of aromatic and aliphatic thiols. Aryl and alkenyl tosylates are also well tolerated, demonstrating, for the first time, to be competent electrophilic partners in Ni-catalyzed C?S bond formation. The chemoselective functionalization of the C?I bond in the presence of a C?Cl bond allows for designing site-selective tandem C?S/C?N couplings. The formation of the two C-heteroatom bonds takes place in a single operation and represents a rare example of dual electrophile/nucleophile chemoselective process.

A Visible-Light-Harvesting Covalent Organic Framework Bearing Single Nickel Sites as a Highly Efficient Sulfur–Carbon Cross-Coupling Dual Catalyst

Covalent Organic Frameworks (COFs) have recently emerged as light-harvesting devices, as well as elegant heterogeneous catalysts. The combination of these two properties into a dual catalyst has not yet been explored. We report a new photosensitive triazine-based COF, decorated with single Ni sites to form a dual catalyst. This crystalline and highly porous catalyst shows excellent catalytic performance in the visible-light-driven catalytic sulfur–carbon cross-coupling reaction. Incorporation of single transition metal sites in a photosensitive COF scaffold with two-component synergistic catalyst in organic transformation is demonstrated for the first time.