22865-52-7

Usage

Uses

Used in Chemical Synthesis Industry:
4-[(4-METHYLPHENYL)SULFANYL]ANILINE is used as a key intermediate in the synthesis of dyes and other organic compounds, contributing to the development of a wide range of colorants and specialty chemicals.
Used in Pharmaceutical Research:
4-[(4-METHYLPHENYL)SULFANYL]ANILINE is utilized as a starting material or building block in the research and development of new pharmaceuticals, given its potential for biological applications and its unique chemical structure.
Used in Material Science:
In the field of material science, 4-[(4-METHYLPHENYL)SULFANYL]ANILINE may be employed in the design and synthesis of novel materials with specific properties, such as those with enhanced thermal stability or electrical conductivity, depending on the requirements of the application.

InChI:InChI=1/C13H13NS/c1-10-2-6-12(7-3-10)15-13-8-4-11(14)5-9-13/h2-9H,14H2,1H3

Upstream product

• 22865-48-1 4-nitrophenyl 4-methylphenyl sulfide 
• 10486-08-5 sodium p-thiocresolate 
• 100-00-5 4-chlorobenzonitrile 
• 536-57-2 p-toluene sulfinic acid 
• 103-84-4 Acetanilid 
• 109100-37-0 anilinium p-toluenesulfinate 
• 106-45-6 para-thiocresol 
• 540-37-4 p-aminoiodobenzene 
• 636-98-6 p-nitrobenzene iodide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 62-53-3 aniline 
• 106-40-1 4-bromo-aniline 
• 106-47-8 4-chloro-aniline 
• 3899-96-5 4-methylphenyl tosylate 

Downstream Products

• 104128-50-9 (4-cyanophenyl)(4-methylphenyl)sulfide 
• 339096-10-5 N-[4-(p-tolylthio)phenyl]acetamide 
• 128126-95-4 2-Hydroxy-3,5-diiodo-N-(4-p-tolylsulfanyl-phenyl)-benzamide 
• 126584-81-4 4-Chloro-N-(4-p-tolylsulfanyl-phenyl)-benzamide 
• 38420-78-9 4-Chloracetylamino-4'-methyldiphenylsulfid 
• 25057-75-4 4-methyl-4'-isothiocyanatodiphenyl sulphide 
• 38173-10-3 4-Bromacetylamino-4'-methyldiphenylsulfid 

Relevant academic research and scientific papers

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.

Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides

Redox-active benzimidazolium sulfonamides as thiolating reagents have been developed for reductive C-S bond coupling. The IMDN-SO2R reagent provides a bench-stable cationic precursor to generate a portfolio of highly active N-S intermediates, which can be successfully applied in cross-electrophilic coupling with various organic halides. The employment of an electrophilic sulfur source solved the problem of catalyst deactivation and avoided odorous thiols, featuring practical conditions, broad substrate scope, and excellent tolerance.

Iodine/DMSO-Promoted Selective Direct Arylthiation of Anilines with Thiols under Metal-Free Conditions

An iodine-promoted divergent thiolation of unprotected anilines with thiols for the synthesis of sulfide anilines has been described. The combinational use of I2 and DMSO played an important role to realize this kind of transformation without the aid of a

Flavin/I2 catalyzed aerobic oxidative C–H sulfenylation of anilines

A flavin/I2 catalyzed aerobic oxidative C–H sulfenylation of anilines with thiols under mild reaction conditions is presented for the first time. This metal-free reaction provides an atom-economic pathway to prepare various aryl sulfides with outstanding functional group compatibility. Moreover, it consumes molecular oxygen as the only terminal oxidant and produces environmentally-friendly H2O as the only byproduct.

TBAI-mediated sulfenylation of arenes with arylsulfonyl hydrazides in DPDME

An efficient TBAI (tetrabutylammonium iodide)-mediated C–H sulfenylation of arenes with arylsulfonyl hydrazides in dipropylene glycol dimethyl ether (DPDME) was described. Various electron-rich arenes were applicable in the reaction, such as naphthylamine, naphthol, aniline, indole, pyrrole, and imidaz o [1,2-a] pyridine. A wide range of the aryl sulfides were obtained with good functional group tolerance. This method features green reaction conditions (odorless and easily available sulfur reagent, recyclable TBAI, and DPDME as solvent), and broad substrate scope. The synthetic potential is demonstrated by gram-scale synthesis and downstream transformations. The mechanism studies show that the reaction is achieved through electrophilic substitution process, and diaryl disulfide may be the main intermediate.

Method for synthesis of diaryl thioether compound without transition metal catalysis

The invention discloses a method for synthesis of a diaryl thioether compound without transition metal catalysis. The method includes: in the presence of a riboflavin catalyst, an iodine source, and an oxidant, reacting a compound shown as formula (1) or a compound shown as formula (4) with a compound shown as formula (2) in a solvent at 30-100DEG C for 1-40h, and subjecting the reaction solutionto post-treatment to obtain the diaryl thioether compound shown as formula (3) or formula (5). The reaction equation is shown as the specification, in the formula (1)-formula (5), R1 is selected fromC1-C4 alkyl, aryl, C1-C4 alkoxy, halogen, halogen-substituted C1-C4 alkyl, aryl, nitro, cyano, amino, or heterocyclic mercaptan; R2, R3, and R4 are independently selected from one of H, C1-C4 alkyl, halogen-substituted C1-C4 alkyl, and aryl respectively; R5 and R6 are independently selected from C1-C4 alkyl respectively, and Y represents element O. The method provided by the invention uses a riboflavin catalyst to replace a transition metal to synthesize the diaryl thioether compound, and has the advantages of green reaction, mild conditions, good substrate universality, high yield and the like.

CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides

In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.

Crystallographic and SAR analyses reveal the high requirements needed to selectively and potently inhibit SIRT2 deacetylase and decanoylase

A high-quality X-ray crystal structure reveals the mechanism of compound 1a inhibiting SIRT2 deacetylase and decanoylase. Structure-activity relationship (SAR) analysis of the synthesized derivatives of 1a reveals the high requirements needed for selectiv

Regioselective thiolation of electron rich arenes and heterocycles in recyclable catalytic media

A convenient and novel approach has been developed for the synthesis of unsymmetrical diaryl sulfides by the reaction of sulfonyl hydrazides with phenols using a [Bmim][Br] ionic liquid through the formation of C-S bonds. The reaction has further been extended to indole, β-naphthol and aromatic amine moieties. This protocol offers a new, versatile and greener approach for thiolation of natural phenols (monoterpenes)/aromatic phenols/β-naphthols/aromatic amines and indoles without using any catalyst. A broad range of functional groups were well tolerated in this reaction system.

Odorless, Regioselective Synthesis of Diaryl Sulfides and α-Thioaryl Carbonyls from Sodium Arylsulfinates via a Metal- Free Radical Strategy in Water

Regioselective arylthiolations of aromatic amines, arenols and ketones via C–H bond functionalization have been achieved with I2and PPh3in an aqueous system, whereby arylsulfenyl radicals are in situ generated from odorless sodium arylsulfinates. The arylsulfenyl radicals can react with free anilines containing electron-withdrawing groups and complex substrates (estrone and progesterone). Further experiments and quantum chemical calculations were also performed to deduce a mechanism for the formation of arylsulfenyl radicals. (Figure presented.).