599-86-0

Basic information

• Product Name: N-(p-tolyl)-p-toluenesulphonamide
• Synonyms: N-(p-tolyl)-p-toluenesulphonamide;N-(p-Tolyl)-p-toluenesulfonamide;4'-Methyl-p-toluenesulfoanilide;N-(4-Methylphenyl)-4-methylbenzenesulfonamide;N-(p-Tolyl)-4-methylbenzenesulfonamide;4-methyl-N-(4-methylphenyl)benzenesulfonamide
• CAS NO: 599-86-0
• Molecular Formula: C₁₄H₁₅NO₂S
• Molecular Weight: 261.3394
• EINECS: 209-975-9
• Mol File: 599-86-0.mol
• Article Data: 101

Chemical Properties

• Boiling Point: 403.7°Cat760mmHg
• Flash Point: 198°C
• Appearance: /
• Density: 1.237g/cm³
• Vapor Pressure: 9.97E-07mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: N-(p-tolyl)-p-toluenesulphonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(p-tolyl)-p-toluenesulphonamide(599-86-0)
• EPA Substance Registry System: N-(p-tolyl)-p-toluenesulphonamide(599-86-0)

Safety Data

• Hazardous Substances Data: 599-86-0(Hazardous Substances Data)

Usage

General Description

N-(p-tolyl)-p-toluenesulphonamide, also known as PTSA, is a white crystalline solid that is commonly used as a strong acid catalyst in various chemical reactions. It is a sulfonamide compound with the molecular formula C14H14N2O2S. PTSA is widely used in the synthesis of organic compounds, polymerization processes, and in the production of pharmaceuticals and agrochemicals. It is also used as a dye and ink additive, as well as a corrosion inhibitor in industrial applications. Due to its acidic properties and catalytic activity, PTSA is considered an important reagent in the field of organic chemistry.

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

Upstream product

• 127-09-3 sodium acetate 
• 106-49-0 p-toluidine 
• 98-59-9 p-toluenesulfonyl chloride 
• 54856-34-7 C₁₄H₁₉N₃O₃S 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 108-88-3 toluene 
• 941-55-9 4-toluenesulfonyl azide 
• 5720-05-8 4-methylphenylboronic acid 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 4083-64-1 Tosyl isocyanate 
• 262373-15-9 4-methyl-2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 14034-62-9 4-methylanilinium p-toluenesulfonate 
• 78486-46-1 1-(N-benzoyl-p-methylphenyloamino)-3-(p-methylphenylimino)-1-propene 
• 106-38-7 para-bromotoluene 

Downstream Products

• 61613-24-9 3,3,5-trimethyl-2-p-tolyl-2,3-dihydro-benzo[d]isothiazole 1,1-dioxide 
• 115964-36-8 4-Methyl-N-phenylacetyl-N-p-tolyl-benzenesulfonamide 
• 93009-23-5 N-acetyl-N-(toluene-4-sulfonyl)-p-toluidine 
• 95793-84-3 N,N-bis(p-tolylsulfonyl)-4-methylaniline 
• 2903-37-9 N-(2-chloro-4-methylphenyl)-4-methylbenzenesulfonamide 
• 88-44-8 2-Amino-5-methylbenzenesulfonic acid 
• 4284-58-6 4-methyl-2-[(4-methylphenyl)sulfonyl]aniline 
• 852292-23-0 N-(2-iodo-4-methylphenyl)-4-methylbenzenesulfonamide 
• 137236-13-6 toluene-4-sulfonic acid-(4-methyl-2,6-dinitro-anilide) 
• 106-49-0 p-toluidine 
• 104-15-4 toluene-4-sulfonic acid 
• 39967-87-8 3-Aminotoluol-2-sulfonsaeure 
• 98-59-9 p-toluenesulfonyl chloride 
• 109562-55-2 toluene-4-sulfonic acid-(N-butyl-p-toluidide) 

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.).

Ligand-Regulated Palladium-Catalyzed Regiodivergent Hydroarylation of the Distal Double Bond of Allenamides with Aryl Boronic Acid

The ligand-regulated regiodivergent hydroarylation of the distal double bond of allenamides with aryl boronic acid was achieved in the presence of palladium(II) catalysts, delivering a variety of functionalized enamide with excellent E selectivity and Markovnikov/anti-Markovnikov selectivity. Two possible coordination intermediates were proposed to be responsible for the regiodivergent hydroarylation: (1) The coordination Intermediate I, which was proposed to be formed through the coordination of MeCN, distal double bond, phenyl to palladium, led to the aryl group away from the Intermediate I, inducing excellent E selectivity and anti-Markovnikov selectivity. (2) A switch of regioselectivity to 1,2-Markovnikov hydroarylation was obtained using bidentate phosphine ligand (dppf or Xantphos). The formed coordination Intermediate II led to the N-tether away from the Intermediate II and at the trans position of aryl, resulting in excellent E selectivity and Markovnikov selectivity. Meanwhile, tentative investigation on the mechanism proved that the hydron source of this hydroarylation is more likely to be boronic acid. The transmetallation between aryl boronic acid and palladium catalyst was the initial step of this transformation.

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.