80-39-7

Basic information

• Product Name: N-Ethyl-p-toluenesulfonamide
• Synonyms: Benzenesulfonamide, N-ethyl-4-methyl-;Ethyl toluenesulfonamide;Ethylp-toluenesulfonamide;n-ethyl-4-methyl-benzenesulfonamid;n-ethyl-4-methylbenzenesulfonamide;N-Ethyl-4-methyl-benzenesulfonamide;n-ethyl-4-toluenesulfonamide;N-Ethyl-p-methylbenzenesulfonamide
• CAS NO: 80-39-7
• Molecular Formula: C₉H₁₃NO₂S
• Molecular Weight: 199.27
• EINECS: 201-275-1
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Protected Amines
• Mol File: 80-39-7.mol

Chemical Properties

• Melting Point: 63-65 °C(lit.)
• Boiling Point: 208 °C745 mm Hg(lit.)
• Flash Point: 141.9 °C
• Appearance: off-white crystalline solid
• Density: 1.26 g/cm3
• Refractive Index: 1.5270 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 11.86±0.50(Predicted)
• Water Solubility: <0.01 g/100 mL at 18℃
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: N-Ethyl-p-toluenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Ethyl-p-toluenesulfonamide(80-39-7)
• EPA Substance Registry System: N-Ethyl-p-toluenesulfonamide(80-39-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 80-39-7(Hazardous Substances Data)

Usage

Uses

Used in Dental Materials:
N-Ethyl-p-toluenesulfonamide is used as a resin carrier in dental materials for isolating cavities below restorations. Its role in dental applications is crucial for ensuring the proper setting and bonding of dental resins, contributing to the overall effectiveness and durability of dental restorations.
Used in Plasticizers:
N-Ethyl-p-toluenesulfonamide is utilized as a plasticizer in various materials such as polyvinyl alcohol lacquers, polyamides, and cellulose acetate. As a plasticizer, it helps to increase the flexibility, workability, and processability of these materials, making them more suitable for a wide range of applications.
Used in Chemical Synthesis:
N-Ethyl-p-toluenesulfonamide is employed as a reagent in the sulfonamidation of imidazopyridines. This chemical process is essential for the synthesis of various pharmaceutical compounds and organic molecules, highlighting the importance of N-Ethyl-p-toluenesulfonamide in the field of organic chemistry and drug development.

Air & Water Reactions

Insoluble in water.

Fire Hazard

Flash point data for N-Ethyl-p-toluenesulfonamide are not available; however, N-Ethyl-p-toluenesulfonamide is probably combustible.

InChI:InChI=1/C9H13NO2S/c1-3-8-6-7(2)4-5-9(8)10-13(11)12/h4-6,13H,3H2,1-2H3,(H,10,11,12)

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 
• 75-04-7 ethylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 16548-07-5 ethylsulfamoyl chloride 
• 937-12-2 4-tolyltrimethylstannane 
• 74-85-1 ethene 
• 29981-92-8 1-tosyl-3-methyl-imidazolium chloride 
• 141-43-5 ethanolamine 
• 155164-58-2 2-(4-methylbenzenesulfonyl)-4,5-dichloropyridazin-3-one 
• 21567-23-7 N-ethyl-N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide 
• 349098-36-8 N-ethyl cyclohexylbenzene sulfonamide 
• 64-17-5 ethanol 
• 109-63-7 boron trifluoride diethyl etherate 

Downstream Products

• 10285-92-4 N-ethyl-N-butyl-toluene-4-sulfonamide 
• 4703-19-9 N,N-diphenyl-p-toluenesulfonamide 
• 649-15-0 N,N-diethyl-4-methylbenzenesulfonamide 
• 37477-72-8 C₁₀H₁₃ClN₂O₅S₂ 
• 56059-57-5 N-Ethyl-N-thallium(I)-4-methylphenylsulfonamid 
• 71173-13-2 N-ethyl-N-p-toluenesulfonylacetamide 
• 5228-67-1 N-Aethyl-N--formamid-diaethylacetal 
• 58754-95-3 N-(2,2-dimethoxyethyl)-p-toluenesulfonamide 
• 87010-92-2 C₉H₁₄N₂O₂S 
• 113812-28-5 N-ethyl-N-(3-chloropropyl)-p-toluenesulfonamide 
• 53839-01-3 1-<3.4-Difluorphenyl>-2-aethylaminoaethanol 
• 259656-68-3 N-[(4R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl]-N-ethyl-p-toluenesulfonamide 
• 309974-76-3 2-dec-9-enyl-N-ethyl-4-methyl-benzenesulfonamide 
• 70-55-3 toluene-4-sulfonamide 

Relevant articles and documents

Chemoselective Cleavage of Acylsulfonamides and Sulfonamides by Aluminum Halides

The chemoselective cleavage of C-N bonds of amides, sulfonamides, and acylsulfonamides by aluminum halides is described. AlCl3and AlI3display complementary reactivities toward N-alkyl and N-acyl moieties. N-Alkylacylsulfonamides, sec

Manganese-Catalyzed N-F Bond Activation for Hydroamination and Carboamination of Alkenes

A visible-light-promoted method for generating amidyl radicals from N-fluorosulfonamides via a manganese-catalyzed N-F bond activation strategy is reported. This protocol employs a simple manganese complex, Mn2(CO)10, as the precatalyst and a cheap silane, (MeO)3SiH, as both the hydrogen-atom donor and the F-atom acceptor, enabling intramolecular/intermolecular hydroaminations of alkenes, two-component carboamination of alkenes, and even three-component carboamination of alkenes. A wide range of valuable aliphatic sulfonamides can be readily prepared using these practical reactions.

Nickel/Photoredox Dual Catalytic Cross-Coupling of Alkyl and Amidyl Radicals to Construct C(sp3)-N Bonds

The construction of C(sp3)-N bonds via direct radical-radical cross-coupling under benign conditions is a desirable but challenging approach. Herein, the cross-coupling of alkyl and amidyl radicals to build aliphatic C-N bonds in a concise, mild, and oxid

Synthesis of N-substituted sulfonamides containing perhalopyridine moiety as bio-active candidates

A series of new halogenated aryl sulfonamides, as bio-active candidates, was synthesized from the reaction of the corresponding aryl sulfonamides with pentafluoro- and pentachloropyridines. Surprisingly, unlike aryl sulfonamides, the reaction of sulfamides with pentafluoro- and pentachloropyridines gave unexpected bis-perfluoro(chloro)pyridin-4-ylamines.

Transition-Metal-Free One-Step Synthesis of Ynamides

A robust transition-metal-free one-step strategy for the synthesis of ynamides from sulfonamides and (Z)-1,2-dichloroalkenes or alkynyl chlorides is presented. This method is not only effective for internal ynamides but also amenable for terminal ynamides. Various functional groups, even the vinyl moiety, are compatible, and thus, this strategy offers the opportunity for further functionalization.

Manganese-Catalyzed N-Alkylation of Sulfonamides Using Alcohols

An efficient manganese-catalyzed N-alkylation of sulfonamides has been developed. This borrowing hydrogen approach employs a well-defined and bench-stable Mn(I) PNP pincer precatalyst, allowing benzylic and simple primary aliphatic alcohols to be employed as alkylating agents. A diverse range of aryl and alkyl sulfonamides undergoes mono-N-alkylation in excellent isolated yields (32 examples, 85% average yield).

Metal-free C-H sulfonamidation of pyrroles by visible light photoredox catalysis

We report a one-step procedure for the preparation of N-(2-pyrrole)-sulfonamides from sulfonamides and pyrroles. The reaction uses visible light, an acridinium dye as photocatalyst and oxygen as the terminal oxidant for the oxidative C-N bond formation; structures of several reaction products were confirmed by X-ray structure analysis. The reaction is selective for pyrroles, due to the available oxidation power of the photocatalyst and the required stability of the carbocation intermediate under the reaction conditions.

The mechanism of alkene elimination from protonated toluenesulphonamides generated by electrospray ionisation

The positive ion electrospray mass spectra of a range of sulphonamides of general structure CH3C6H4SO2NHR1 [R1 = CnH2n+1 (n = 1-7), CnH2n-1 (n = 3, 4), C6H5, C6H5CH2 and C6H5CH(CH3)] and CH3C6H4SO2NR1R2 [R1, R2 = CnH2n+1 (n = 1-8)] are reported and discussed. The protonated sulphonamides derived from saturated primary and secondary aliphatic amines generally fragment to only a limited extent unless energised by collision. Two general fragmentations are observed: firstly, elimination of an alkene, CnH2n, obtained by hydrogen abstraction from one of the CnH2n+1 alkyl groups on nitrogen; secondly, cleavage to form CH3C6H4SO2+. The mechanism by which an alkene is lost has been probed by studying the variation of the intensity of the [M + H - CnH2n]+ signal with the structure of the alkyl substituent(s) on nitrogen and by monitoring the competition between the loss of different alkenes from protonated unsymmetrical sulphonamides in which two different alkyl groups are attached to nitrogen. This fragmentation is favoured by branching of the alkyl group at the carbon atom directly attached to nitrogen, thus suggesting that it involves a mechanism in which the stability of the cation obtained by stretching the bond connecting the nitrogen atom to the alkyl group is critical. This interpretation also explains the competition between alkene elimination and cleavage to form CH3C6H4SO2+ (and, in some cases, cleavage to form C6H5CH2+ or [C6H5CHCH3]+).

Electrosynthesis of Arylsulfonamides from Amines and Sodium Sulfinates Using H2O-NaI as the Electrolyte Solution at Room Temperature

With H2O as the solvent and NaI as the supporting electrolyte, a green and efficient electrochemical route has been developed to synthesize arylsulfonamides via I2electrogenerated in situ at a graphite anode to promote the reaction of sodium sulfinates with aromatic or aliphatic primary and secondary amines. The target products could be obtained in good to excellent yields at room temperature.

Electrochemical Oxidative Amination of Sodium Sulfinates: Synthesis of Sulfonamides Mediated by NH4I as a Redox Catalyst

An efficient protocol for the synthesis of sulfonamides via the electrochemical oxidative amination of sodium sulfinates has been developed. The chemistry proceeds in a simple undivided cell employing a substoichiometric amount of NH4I that serves both as a redox catalyst and a supporting electrolyte; in this manner additional conducting salt is not required. A wide range of substrates, including aliphatic or aromatic secondary and primary amines, as well as aqueous ammonia, proved to be compatible with the protocol. Scale-up was possible, thereby demonstrating the practicality of the approach. The electrolytic process avoids the utilization of external oxidants or corrosive molecular iodine and therefore represents an environmentally benign means by which to achieve the transformation.