24535-57-7

Basic information

• Product Name: 1-bromo-4-(4-chlorophenyl)sulfanylbenzene
• Synonyms: 1-bromo-4-(4-chlorophenyl)sulfanylbenzene;(4-BROMOPHENYL)(4-CHLOROPHENYL)SULFANE
• CAS NO: 24535-57-7
• Molecular Formula: C₁₂H₈BrClS
• Molecular Weight: 299.62
• Mol File: 24535-57-7.mol

Chemical Properties

• Boiling Point: 395.7°C at 760 mmHg
• Flash Point: 193.1°C
• Appearance: /
• Density: 1.58g/cm³
• Vapor Pressure: 4.1E-06mmHg at 25°C
• Refractive Index: 1.689
• CAS DataBase Reference: 1-bromo-4-(4-chlorophenyl)sulfanylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-bromo-4-(4-chlorophenyl)sulfanylbenzene(24535-57-7)
• EPA Substance Registry System: 1-bromo-4-(4-chlorophenyl)sulfanylbenzene(24535-57-7)

Safety Data

• Hazardous Substances Data: 24535-57-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-bromo-4-(4-chlorophenyl)sulfanylbenzene is used as an intermediate in the synthesis of pharmaceuticals for its ability to act as a building block for more complex organic molecules, contributing to the development of new drugs.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 1-bromo-4-(4-chlorophenyl)sulfanylbenzene is used as an intermediate in the synthesis of agrochemicals, playing a role in the creation of new compounds for agricultural applications.
Used in Research and Development:
1-bromo-4-(4-chlorophenyl)sulfanylbenzene is also utilized in the research and development of new chemical compounds, serving as a key component in the exploration of novel chemical entities and their potential applications.

InChI:InChI=1/C12H8BrClS/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H

Upstream product

• 16913-61-4 dimethyl-dithiocarbamic acid 4-chloro-phenyl ester 
• 106-40-1 4-bromo-aniline 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 106-53-6 para-bromobenzenethiol 
• 5467-74-3 4-Bromophenylboronic acid 
• 106-54-7 p-Chlorothiophenol 
• 637-87-6 1-Chloro-4-iodobenzene 
• 21969-12-0 4-bromophenyl 4′-nitrophenyl sulfide 
• 18620-02-5 (4-bromophenyl)magnesium bromide 
• 589-87-7 1,4-bromoiodobenzene 
• 7647-01-0 hydrogenchloride 
• 7727-15-3 aluminium bromide 
• 108-90-7 chlorobenzene 

Downstream Products

• 106-39-8 bromochlorobenzene 
• 106-37-6 1.4-dibromobenzene 
• 1451093-23-4 {4-[4-(4-chloro-phenylsulfanyl)-phenyl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester 
• 1451093-63-2 {6-chloro-4-[4-(4-chloro-phenylsulfanyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester 
• 23055-77-8 4'-chloro-4-bromo-biphenyl 
• 24535-50-0 1-bromo-4-((4-chlorophenyl)sulfinyl)benzene 
• 1451093-62-1 {6-chloro-4-[4-(4-chloro-benzenesulfonyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid 
• 1451093-64-3 {6-chloro-4-[4-(4-chloro-benzenesulfonyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester 
• 1451093-22-3 {4-[4-(4-chloro-benzenesulfonyl)-phenyl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid 
• 1451093-24-5 {4-[4-(4-chloro-benzenesulfonyl)-phenyl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester 
• 65082-45-3 1-(4-chlorophenylsulfonyl)-4-bromobenzene 

Relevant articles and documents

A template free protocol for fabrication of a Ni(ii)-loaded magnetically separable nanoreactor scaffold for confined synthesis of unsymmetrical diaryl sulfides in water

In the present report, an environmentally benign magnetically recoverable nickel(ii)-based nanoreactor as a heterogeneous catalyst has been developedviaa template free approach. The catalytic performance of the synthesized catalyst is assessed in the confined oxidative coupling of arenethiols with arylhydrazines to form unsymmetrical diaryl sulfides under aerobic conditions. The salient features of our protocol include oxidant- and ligand-free conditions, use of water as a green solvent, room temperature and formation of nitrogen and water as the only by-products. Moreover, a broad range of functional groups are tolerated well and provide the corresponding diaryl sulfides in moderate to good yields. Moreover, the heterogeneous nature of the catalyst permits facile magnetic recovery and reusability for up to seven runs, making the present protocol highly desirable from industrial and environmental standpoints.

Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: Synthesis of diarylsulfides

A NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air. This methodology is reliable and offers a mild and easy to operate process for the synthesis of arylthioethers, which are essential compounds with applications in the pharmaceutical and agricultural industries. This method avoids the use of expensive transition metals, such as Pd, Ir or Rh, sophisticated ligands and elevated temperatures. It also has a wide substrate scope (55 examples) and provides products in good to excellent yields (72-93%).

Metal-Free Cercosporin-Photocatalyzed C-S Coupling for the Selective Synthesis of Aryl Sulfides under Mild Conditions

Aryl sulfides are important motifs of bioactive molecules, which are generally synthesized by transition metal-based coupling reactions under harsh conditions. Herein, we developed a new method that visible light along with cercosporin, produced by liquid fermentation and functioned as a cost-effective and environmentally friendly photocatalyst, prompted the selective synthesis of aryl sulfides through C–S coupling of thiols and diazonium salts under mild conditions. Furthermore, this method can also be performed with a great conversion by the direct use of cercosporin-containing fermentation supernatant as catalytic system without organic solvent extraction.

Aryldithiocarbamates as thiol alternatives in Cu-catalyzed C(aryl)-S coupling reactions using aryldiazonium tetrafluoroborate salts

An efficient method for the synthesis of unsymmetrical diaryl sulfides has been developed by the C-S cross coupling of aryldithiocarbamates and aryldiazonium salts in the presence of CuI-2,2′-bipyridine and Zn. Aryldithiocarbamate compounds have been used here as thiol substitutes. The protocol shows wide substrate scope and good yields of the products.

SUBSTITUTED NAPHTHYLACETIC ACIDS

The invention is concerned with the compounds of formula (I): and pharmaceutically acceptable salts thereof, wherein R1, R2, R3 and X are defined in the detailed description and claims. In addition, the present invention r

Recyclable heterogeneous supported copper-catalyzed coupling of thiols with aryl halides: base-controlled differential arylthiolation of bromoiodobenzenes

Alumina-supported copper sulfate efficiently catalyzes the 5-arylation of aromatic, heteroaromatic and aliphatic thiols with aryl as well as heteroaryl halides under aerobic, ligand-free conditions. This protocol provides an easy access to a variety of thioethers as well as unsymmetrical bis-thioethers by base-controlled differential coupling of thiols with iodo- and bromo-substituents in an aromatic halide. The catalyst is inexpensive, non-air sensitive, environmentally friendly and recyclable.

Microwave-assisted simple and efficient ligand free copper nanoparticle catalyzed aryl-sulfur bond formation

A new protocol for the coupling of aryl iodides with thiophenols and alkanethiols catalyzed by copper nanoparticles under ligand-free condition has been developed. A variety of functionalized aryl sulfides are prepared in excellent yields under microwave irradiation for 5-7 min. A plausible radical mechanism has been suggested.

A mild and efficient copper-catalyzed coupling of aryl iodides and thiols using an oxime-phosphine oxide ligand

A mild and efficient copper-catalyzed system for the coupling of aryl iodides and thiols was developed using a readily prepared and highly stable oxime-phosphine oxide ligand. Good to excellent yields were obtained.

CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands

Novel mild conditions for the CuI-catalyzed coupling reactions of aryl iodides and bromides with aliphatic and aromatic thiols using amino acids as the ligand are reported.

Ring-opening reactions of 5-(aryl)thianthrenium bromides with aryl thiolates

A series of 5-(aryl)thianthrenium bromides (6a-e) with aryl (Ar) groups phenyl (a), p-tolyl (b), p-anisyl (c), p-chlorophenyl (d) and p-bromophenyl (e) was prepared by reaction of thianthrene 5-oxide with the appropriate Grignard reagent ArMgBr. Reactions of 6a-e with aryl thiolates (Ar′SNa, Ar′ = phenyl, p-tolyl and p-chlorophenyl, 7a-c) were carried out in MeCN at room temperature. Products from 6a-c were a small amount of arene [benzene (8a) and toluene (8b)], and substantial amounts of ArSAr′ (9), thianthrene (Th) and a trisulfide, namely a 2-(ArS)-2′-(Ar′S)-diphenyl sulfide (10). Products from reactions of 6d,e were smaller amounts of 9 and 10 but substantial amounts of 1,4-di(Ar′S)benzene (11) and a tetrasulfide (12a-c). The reactions that lead to products 9-12 are attributed to ligand coupling (LC) pathways in sulfuranes formed by attack of Ar′S- at the sulfonium S atom of 6. In the formation of 11 and 12 the halogen atom (CI, Br) is first displaced from 6d,e by Ar′S-, giving a new thianthrenium ion (14) from which sulfurane formation (15) follows. Products 10 and 12 result from opening of the thianthrenium ring of sulfuranes 13 and 15 through LC. Products were assayed with a combination of GC and isolation with TLC, and were identified with a combination of GC (authentic compounds), x-ray crystallography (10a), elemental analyses and high-resolution mass spectrometry. The reactions of 6 are compared with earlier reactions of 5-(alkoxy)-and 5-(alkyl)thianthrenium salts (1 and 2). Copyright