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

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

Uses

Used in Cosmetics Industry:
N-(o-tolyl)-p-toluenesulphonamide is used as a hardening agent in nail polishes for its ability to provide a durable and long-lasting finish.
Used in Plastics and Resin Production:
In the plastics and resins industry, N-(o-tolyl)-p-toluenesulphonamide is used as a plasticizer and a binding agent, enhancing the flexibility and stability of the final products.
Used in Personal Care Products:
Due to its antimicrobial properties, N-(o-tolyl)-p-toluenesulphonamide is used in the manufacture of antibacterial soaps and other personal care products to provide hygiene benefits.
Used in Pharmaceutical Research:
N-(o-tolyl)-p-toluenesulphonamide has been studied for its potential use in pharmaceuticals, particularly for its enzyme-inhibiting capabilities, indicating a promising direction for future medicinal applications.

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

• 98-59-9 p-toluenesulfonyl chloride 
• 95-53-4 o-toluidine 
• 615-37-2 ortho-methylphenyl iodide 
• 70-55-3 toluene-4-sulfonamide 
• 95-46-5 2-methylphenyl bromide 
• 42096-33-3 o-tolyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 
• 95-48-7 ortho-cresol 
• 95-49-8 2-methylchlorobenzene 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 108-88-3 toluene 
• 83228-40-4 methyl 3-(2-methylanilino)propionate 
• 1422186-08-0 methyl N-tosyl-3-(2-methylanilino)propionate 
• 1422186-13-7 N-tosyl-4-(2-methylanilino)-2-methyl-2-butanol 
• 583-60-8 2-Methylcyclohexanone 

Downstream Products

• 872283-71-1 N-(toluene-4-sulfonyl)-N-o-tolyl-β-alanine 
• 145964-19-8 toluene-4-sulfonic acid-(N-ethyl-o-toluidide) 
• 570-24-1 2-Methyl-6-nitroaniline 
• 7477-94-3 2-methyl-4,6-dinitroaniline 
• 2903-39-1 toluene-4-sulfonic acid-(N-chloro-o-toluidide) 
• 97-15-4 4-methyl-N-(2-methyl-4-nitrophenyl)benzenesulfonamide 
• 408329-33-9 toluene-4-sulfonic acid-(2-methyl-4,6-dinitro-anilide) 
• 6380-09-2 toluene-4-sulfonic acid-(N-methyl-o-toluidide) 
• 156267-23-1 N-(2-Dimethylamino-ethyl)-4-methyl-N-o-tolyl-benzenesulfonamide 
• 114879-46-8 N-(4,5-diisopropyl-2-tolyl)-4-toluenesulfonamide 
• 584-70-3 N-benzoyl-2-methylaniline 

Relevant articles and documents

Lewis Acid Regulated Divergent Catalytic Reaction between Quinone Imine Ketals (QIKs) and 1,3-Dicarbonyl Compounds: Switchable Access to Multiple Products Including 2-Aryl-1,3-Dicarbonyl Compounds, Indoles, and Benzofurans

A catalytic Lewis acid regulated reaction between quinone imine ketals (QIKs) and 1,3-dicarbonyl compounds provides a divergent and tunable approach to a variety of skeletons, including a series of 2-aryl-1,3-dicarbonyl compounds, indoles, and benzofurans. The use of lithium chloride and ferrous bromide gives C3- or C2-alkylation products of the QIKs. The combination of ferrous bromide and trifluoromethanesulfonic acid delivers indole derivatives. Sequential hydrolysis and C3-alkylation occur in the presence of ytterbium (III) trifluoromethanesulfonate and stoichiometric amounts of water. When the reaction is performed with trifluoromethanesulfonic acid and stoichiometric amounts of water, benzofuran is obtained. This protocol utilizes mild conditions, exhibits regio- and chemoselectivity, and has broad functional group tolerance. (Figure presented.).

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.

Method for synthesizing P-chloroO-toluidine

The invention discloses a method for synthesizing p-chloroo-toluidine, which comprises the following steps: synthesizing o-toluidine and a protective agent in an organic solvent to obtain an amino-protected intermediate. The amino protected intermediate is added into hydrochloric acid, an oxidant is added for chlorination reaction, and a chlorination product is obtained. The chlorinated product is removed and the amino protecting group is removed to give p-chloroo-toluidine. The method for synthesizing p-chloroo-toluidine provided by the invention is high in yield, simple to operate, less in three wastes, high in product content and good in quality, and can be suitable for industrial mass production.

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.

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.

KCC-1 aminopropyl-functionalized supported on iron oxide magnetic nanoparticles as a novel magnetic nanocatalyst for the green and efficient synthesis of sulfonamide derivatives

A new magnetic nanocatalyst (Fe3O4@KCC-1-npr-NH2) was synthesized directly through the reaction of Fe3O4@KCC-1 with (3-aminopropyl) triethoxysilane (APTES) using a hydrothermal protocol. Prepared nanocomposite was used as a magnetically reusable nanocatalyst for an efficient synthesis of a broad range of sulfonamide derivatives in water as a green solvent at room temperature and the products are collected by filtration with excellent yields (85–97%). The nanocatalyst could be remarkably recovered and reused after ten times without any significant decrease in activity. This mild and simple synthesis method offers some advantages including short reaction time, high yield and simple work-up procedure.

Synthetic method for 2-amino-4'-fluoro-benzophenone

The invention discloses a synthetic method for 2-amino-4'-fluoro-benzophenone. The method comprises the following steps: subjecting o-toluidine and tosyl chloride to an amidation reaction to obtain 4-methyl-N-(2-methylphenyl) benzenesulfonamide; then performing chlorination by a chlorine gas, producing a Friedel-Crafts reaction with fluorobenzene, and obtaining N-(2-(4-fluorobenzoyl)phenyl)-4-toluenesulfonamide; and finally obtaining the 2-amino-4'-fluoro-benzophenone by deprotection of concentrated sulfuric acid. The synthetic method is cheap and easily available in starting material, is lowin cost, is convenient to operate, is suitable for industrial production, is green and environmentally friendly in synthetic route, and is high in yield, and the purity of the 2-amino-4'-fluoro-benzophenone obtained by preparation is good.

Lewis Base Promoted, Direct 1,4-Conjugate Addition to Quinone Imine Ketals: Efficient Access to Unsymmetrical Diaryl Sulfones

An alternative approach with eco-friendliness and high efficiency for the preparation of unsymmetrical diaryl sulfones has been developed. The strategy takes advantage of the reaction of sulfonyl hydrazides with quinone imine ketals catalyzed by DABCO (triethylenediamine) in ethanol. This transformation proceeds via a Lewis base promoted, direct 1,4-conjugate addition/sulfonylation/alcohol elimination reaction sequence. The protocol provides an efficient approach to access an array of diverse unsymmetrical diaryl and heterodiaryl sulfones, aryl alkyl sulfones and aryl vinyl sulfones in good to excellent yields.

Characteristic Hydrogen Bonding Observed in the Crystals of Aromatic Sulfonamides: 1D Chain Assembly of Molecules and Chiral Discrimination on Crystallization

N-Phenylbenzenesulfonamides exist preferentially in (+)- or (-)-synclinal conformations, which place the aromatic rings at both ends in the same direction with a twist. We have systematically analyzed the crystal structure of secondary aromatic sulfonamides bearing methyl, ethyl, and/or methoxy groups on the benzene rings. Intermolecular hydrogen bonding between the sulfonamide protons and sulfonyl oxygens was observed in 81 out of 85 crystals. The intermolecular hydrogen-bonding patterns could be classified into four types, i.e. Dimeric, Zigzag, Helical, and Straight patterns, with retention of the synclinal conformation of the sulfonamide moiety. We investigated the relationship between the hydrogen-bonding pattern and the proportion of the compounds that show chiral crystallization. On the basis of our classification of the intermolecular hydrogen bonds of aromatic sulfonamides, the crystals with Dimeric and Zigzag patterns, which both have enantiomeric synclinal conformers, intrinsically become achiral, except for kryptoracemates. In contrast, a high proportion of compounds with Helical or Straight patterns in the crystals showed chiral crystallization. Our classification is useful for discussion regarding the chirality of molecular assemblies, on the basis of the conformational chirality of the molecules in the crystal.

Copper-catalyzed redox coupling of nitroarenes with sodium sulfinates

A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.