22865-52-7

Basic information

• Product Name: 4-[(4-METHYLPHENYL)SULFANYL]ANILINE
• Synonyms: 4-[(4-METHYLPHENYL)SULFANYL]ANILINE;4-[(4-methylphenyl)sulfanyl]phenylamine;4-[(4-Methylphenyl)thio]aniline
• CAS NO: 22865-52-7
• Molecular Formula: C₁₃H₁₃NS
• Molecular Weight: 215.31
• Mol File: 22865-52-7.mol
• Article Data: 25

Chemical Properties

• Melting Point: 73-75,5°C
• Boiling Point: 395.8°Cat760mmHg
• Flash Point: 193.2°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 1.79E-06mmHg at 25°C
• Refractive Index: 1.658
• CAS DataBase Reference: 4-[(4-METHYLPHENYL)SULFANYL]ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(4-METHYLPHENYL)SULFANYL]ANILINE(22865-52-7)
• EPA Substance Registry System: 4-[(4-METHYLPHENYL)SULFANYL]ANILINE(22865-52-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 22865-52-7(Hazardous Substances Data)

Usage

General Description

4-[(4-Methylphenyl)sulfanyl]aniline is a chemical compound with the molecular formula C13H13NS. It is a member of the aniline class of organic compounds and contains a sulfur atom bonded to a phenyl group and an amine group. 4-[(4-METHYLPHENYL)SULFANYL]ANILINE is commonly used in the synthesis of dyes and other organic compounds, and has been studied for its potential pharmaceutical and biological applications. It is a white to off-white solid at room temperature and is soluble in organic solvents such as ethanol and acetone. 4-[(4-Methylphenyl)sulfanyl]aniline should be handled and stored with appropriate safety precautions due to its potential health hazards.

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 
• 722-27-0 bis(4-aminophenyl)disulfide 
• 624-31-7 4-tolyl iodide 
• 103-19-5 di(p-tolyl) disulfide 
• 62-53-3 aniline 
• 1193-02-8 4-aminotiophenol 

Downstream Products

• 104128-50-9 (4-cyanophenyl)(4-methylphenyl)sulfide 
• 339096-10-5 N-[4-(p-tolylthio)phenyl]acetamide 
• 37930-89-5 4-(4-Methylphenylthio)-trifluormethansulfonanilid 
• 54456-59-6 1-Methyl-3-(4-p-tolylsulfanyl-phenyl)-urea 
• 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 
• 111453-15-7 4-amino-4'-methyldiphenylsulphide 

Relevant articles and documents

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.

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

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.