80-28-4

Basic information

• Product Name: N-(o-tolyl)-p-toluenesulphonamide
• Synonyms: N-(o-tolyl)-p-toluenesulphonamide;4-Methyl-N-(2-methylphenyl)benzenesulfonamide;N-(2-Methylphenyl)-p-toluenesulfonamide;N-(o-Tolyl)-4-methylbenzenesulfonamide;P-TOLUENESULFONO-O-TOLUIDIDE;4-methyl-N-(o-tolyl)benzenesulfonamide
• CAS NO: 80-28-4
• Molecular Formula: C₁₄H₁₅NO₂S
• Molecular Weight: 261.3394
• EINECS: 201-267-8
• Mol File: 80-28-4.mol
• Article Data: 46

Chemical Properties

• Boiling Point: 398.1 °C at 760 mmHg
• Flash Point: 194.5 °C
• Appearance: /
• Density: 1.237 g/cm³
• Vapor Pressure: 1.51E-06mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: N-(o-tolyl)-p-toluenesulphonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(o-tolyl)-p-toluenesulphonamide(80-28-4)
• EPA Substance Registry System: N-(o-tolyl)-p-toluenesulphonamide(80-28-4)

Safety Data

• Hazardous Substances Data: 80-28-4(Hazardous Substances Data)

Usage

General Description

N-(o-tolyl)-p-toluenesulphonamide, also known as tosylamide, is a chemical compound that is commonly used as a hardening agent in nail polishes. It is a white crystalline powder that is insoluble in water but soluble in most organic solvents. Tosylamide is also used as a plasticizer and as a binding agent in the production of various polymers and resins. Furthermore, it has antimicrobial properties and is used in the manufacture of antibacterial soaps and other personal care products. Additionally, tosylamide has been studied for its potential use in pharmaceuticals due to its ability to inhibit certain enzymes. It is considered to be relatively safe for use in cosmetic and personal care products when used in accordance with regulatory guidelines.

InChI:InChI=1/C14H15NO2S/c1-11-7-9-13(10-8-11)18(16,17)15-14-6-4-3-5-12(14)2/h3-10,15H,1-2H3

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 108-88-3 toluene 
• 98-09-9 benzenesulfonyl chloride 
• 90312-02-0 N-(2-hydroxymethylphenyl)-4-methylbenzenesulfonamide 
• 5344-90-1 2-Aminobenzyl alcohol 
• 16419-60-6 2-Methylphenylboronic acid 
• 127-65-1 chloroamine-T 
• 941-55-9 4-toluenesulfonyl azide 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 95-53-4 o-toluidine 
• 66107-34-4 2-methylphenyl triflate 
• 95-49-8 2-methylchlorobenzene 
• 88-72-2 1-methyl-2-nitrobenzene 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 872283-71-1 N-(toluene-4-sulfonyl)-N-o-tolyl-β-alanine 
• 6380-09-2 toluene-4-sulfonic acid-(N-methyl-o-toluidide) 
• 145964-19-8 toluene-4-sulfonic acid-(N-ethyl-o-toluidide) 
• 824417-09-6 [(toluene-4-sulfonyl)-o-tolyl-amino]-acetic acid ethyl ester 
• 934560-46-0 N-[2-(4-fluorobenzoyl)phenyl]-4-methylbenzenesulfonamide 
• 42321-55-1 7-methyl-3-phenyl-indolin-2-one 

Relevant articles and documents

Identification of a Nitrenoid Reductive Elimination Pathway in Nickel-Catalyzed C-N Cross-Coupling

Whereas the (bisphosphine)Ni-catalyzed C-N cross-coupling of (hetero)aryl (pseudo)halides with NH nucleophiles represents a useful method for the synthesis of (hetero)anilines, our mechanistic understanding of such cross-couplings is incomplete, especially regarding key C-N reductive elimination steps that are often invoked as turnover-limiting. In this combined experimental and computational study, we provide evidence of a bifurcated C-N reductive elimination pathway for cross-couplings of tBuNH2 and (aryl′)SO2NH2 employing (L1)Ni(aryl)Cl as the precatalyst (L1 = PhPAd-DalPhos). In contrast with direct C-N reductive elimination that proceeds from the nickel alkylamido complex (L1)Ni(aryl)(NHtBu), we provide evidence of a previously undocumented base-promoted pathway involving deprotonation of the nickel sulfonamido complex (L1)Ni(aryl)(NHSO2(aryl′)) to give the anionic nickel nitrenoid species [(L1)Ni(aryl)(NSO2(aryl′))]-, from which C-N reductive elimination occurs preferentially.

Synthesis of magnetic chitosan supported metformin-Cu(II) complex as a recyclable catalyst for N-arylation of primary sulfonamides

The application of chitosan, which has received much attention as a natural polymer and effective support, has many advantages such as biodegradability and biocompatibility. In this study, the immobilization of a copper complex on the magnetic chitosan bearing metformin ligand has been developed through immobilizing structurally defined metformin with long tail of (3-chloropropyl)trimethoxysilane (TMOS). The synthesized Fe3O4-chitosan@metformin-Cu(II) complex (Fe3O4-CS@Met-Cu(II)) was used as an effective, reusable and magnetic catalyst in the N-arylation of different derivatives of primary sulfonamides with arylboronic acids in ethanol. The primary sulfonamides were prepared from the reaction of sulfonyl chlorides with sodium cyanate in water under ultrasonic irradiation. Utilizing a wide variety of substrates in EtOH as a green solvent, high yields of the primary and secondary sulfonamides, easy work-up along with the excellent recovery and reusability of the catalyst, make this process a simple, economic and environmentally benign method. The synthesized Fe3O4-CS@Met-Cu(II) was characterized using various techniques such as XRD (X-ray diffraction), EDS (energy-dispersive X-ray spectroscopy), elemental mapping, TEM (transmission electron microscopy), FESEM (field emission scanning electron microscopy), VSM (vibrating sample magnetometer), ICP-MS (inductively coupled plasma mass spectroscopy), TGA (thermogravimetric analysis) and FT-IR (Fourier-transform infrared spectroscopy) analyses. The catalyst can be recycled and reused 5 times with no considerable loss of catalytic activity.

Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation

The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.