3695-02-1

Basic information

• Product Name: N-BENZYL-N-METHYL-P-TOLUENESULFONAMIDE
• Synonyms: N-BENZYL-N-METHYL-P-TOLUENESULFONAMIDE;N,4-Dimethyl-N-benzylbenzenesulfonamide;N-Benzyl-N,4-dimethylbenzenesulfonamide;N-Methyl-N-benzyl-p-toluenesulfonamide
• CAS NO: 3695-02-1
• Molecular Formula: C₁₅H₁₇NO₂S
• Molecular Weight: 275.36598
• Mol File: 3695-02-1.mol

Chemical Properties

• Boiling Point: 419°Cat760mmHg
• Flash Point: 207.2°C
• Appearance: /
• Density: 1.187g/cm³
• Vapor Pressure: 3.15E-07mmHg at 25°C
• Refractive Index: 1.587
• CAS DataBase Reference: N-BENZYL-N-METHYL-P-TOLUENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYL-N-METHYL-P-TOLUENESULFONAMIDE(3695-02-1)
• EPA Substance Registry System: N-BENZYL-N-METHYL-P-TOLUENESULFONAMIDE(3695-02-1)

Safety Data

• Hazardous Substances Data: 3695-02-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H17NO2S/c1-13-8-10-15(11-9-13)19(17,18)16(2)12-14-6-4-3-5-7-14/h3-11H,12H2,1-2H3

Upstream product

• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 74-88-4 methyl iodide 
• 536-57-2 p-toluene sulfinic acid 
• 3555-71-3 N-benzyl-N-chloromethylamine 
• 100-39-0 benzyl bromide 
• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 100-51-6 benzyl alcohol 
• 26827-38-3 benzyl 2,2,2-trichloroacetate 
• 100-44-7 benzyl chloride 
• 103-67-3 benzyl-methyl-amine 
• 98-59-9 p-toluenesulfonyl chloride 
• 27238-06-8 N-benzyl-N-methylmethanesulfonamide 
• 100-46-9 benzylamine 
• 140-11-4 Benzyl acetate 

Downstream Products

• 103-67-3 benzyl-methyl-amine 
• 622-29-7 N-Benzylidenemethylamine 
• 5694-20-2 N-benzylidenemethylamine 
• 108-88-3 toluene 
• 29823-47-0 N-benzyl-N-methylacetamide 
• 19499-61-7 methyl-(3-nitro-benzyl)-amine 
• 115562-46-4 N-(2'-hydroxybenzyl)-N-methyl-4-toluenesulfonamide 
• 197958-57-9 1-Benzyl-3,3-diisopropyl-1-methyl-urea 
• 81616-14-0 tert-butyl N-benzyl-N-methylcarbamate 
• 17105-71-4 N-methyl-N-benzylformamide 

Relevant articles and documents

Method for selective N-methylation of secondary amide

The invention relates to a method for selective N-methylation of secondary amide. The method is characterized in that the secondary amide is in an organic solvent N, N-dimethyl formamide or dimethyl sulfoxide, trifluoroacetic acid methyl ester serves as a methylation reagent, and reaction is performed in the presence of sodium hydride, potassium tert-butoxide or sodium methylate, so as to obtain aselective N-methylated product. The method has the characteristics that generally a trifluoroacetylation product is produced when the trifluoroacetic acid methyl ester is reacted with amine compounds, however a N-methylated product can be selectively obtained when the trifluoroacetic acid methyl ester is reacted with secondary amide; the method is simple to operate, low in cost, mild in reactionconditions and high in selectivity, and avoids the use of hypertoxic methylation reagents, such as dimethyl sulfate and methyl iodide.

Hypervalent Iodine Mediated Sulfonamide Synthesis

A new metal-free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group-transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram-scale. The reaction mechanism was investigated by ESI-MS and DFT calculations.

Synthesis of aromatic sulfonamides through a copper-catalyzed coupling of aryldiazonium tetrafluoroborates, DABCO·(SO2)2, and N-Chloroamines

A copper-catalyzed aminosulfonylation of aryldiazonium tetrafluoroborates, DABCO·(SO2)2, and N-chloroamines is described. This coupling reaction provides an efficient and simple approach to a wide range of sulfonamides in moderate to good yields under mild conditions. Mechanistic investigation suggests that a radical process and transition-metal catalysis are merged in this tandem reaction.

Potassium tert-butoxide-mediated metal-free synthesis of sulfonamides from sodium sulfinates and N,N-disubstituted formamides

By using formamides as amine sources, a novel and efficient KO-t-Bu mediated amination of sodium sulfinates has been developed. The reaction utilizes readily available starting materials under metal-free conditions, thus providing an alternative and attractive route to sulfonamides.

Preparation method for sulfonamide compound

The invention discloses a preparation method for a sulfonamide compound. The preparation method comprises the following steps: with NIS as an oxidizing agent and potassium tert-butoxide as a base, reacting formamide with sodium arylsulfinate in an organic solvent, and carrying out post-treatment after the reaction is completed so as to obtain the sulfonamide compound. The preparation method uses formamide and sodium arylsulfinate as substrates for synthesis of the sulfonamide compound; the raw materials for the reaction are cheap and easily available; and the preparation method is simple.

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.

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.

DBN hexafluorophosphate salts as convenient sulfonylating and phosphonylating agents

Air-stable N-sulfonyl and N-phosphonyl DBN hexafluorophosphate salts have been synthesised under mild conditions as sulfonylating and phosphonylating agents. These salts are highly efficient in the sulfonylation and phosphonylation of a range of N- and O-nucleophiles to generate sulfonamides, sulfonate esters, phosphoramidates and phosphonate esters in good yields.

Intermolecular hydroaminoalkylation of alkenes and dienes using a titanium mono(formamidinate) catalyst

An easily accessible formamidinate ligand-bearing titanium complex initially synthesized by Eisen et al. is used as catalyst for intermolecular hydroaminoalkylation reactions of unactivated, sterically demanding 1,1- and 1,2-disubstituted alkenes and styr

Synthesis of sulfonamides via I2-mediated reaction of sodium sulfinates with amines in an aqueous medium at room temperature

An efficient I2-mediated approach for the synthesis of sulfonamides at room temperature using water as the solvent has been developed. This method for the synthesis of sulfonamides is quite convenient and environmentally friendly. In addition, the purification procedure of the desired products becomes very easy. This journal is