10504-90-2

Basic information

• Product Name: N-Benzyl-4-chlorobenzenesulfonaMide, 97%
• Synonyms: N-Benzyl-4-chlorobenzenesulfonaMide, 97%
• CAS NO: 10504-90-2
• Molecular Formula: C₁₃H₁₂ClNO₂S
• Molecular Weight: 281.75788
• Mol File: 10504-90-2.mol

Chemical Properties

• Boiling Point: 432.6°Cat760mmHg
• Flash Point: 215.4°C
• Appearance: /
• Density: 1.324g/cm³
• Vapor Pressure: 1.1E-07mmHg at 25°C
• Refractive Index: 1.606
• CAS DataBase Reference: N-Benzyl-4-chlorobenzenesulfonaMide, 97%(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyl-4-chlorobenzenesulfonaMide, 97%(10504-90-2)
• EPA Substance Registry System: N-Benzyl-4-chlorobenzenesulfonaMide, 97%(10504-90-2)

Safety Data

• Hazardous Substances Data: 10504-90-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
N-Benzyl-4-chlorobenzenesulfonamide, 97% is used as a reagent in the synthesis of pharmaceuticals for its ability to facilitate various organic reactions, contributing to the development of new drugs and medicines.
Used in Agrochemical Production:
In the agrochemical industry, N-Benzyl-4-chlorobenzenesulfonamide, 97% is used as a reagent for the synthesis of agrochemicals, aiding in the creation of compounds that protect crops and enhance agricultural productivity.
Used in Fine Chemicals Synthesis:
N-Benzyl-4-chlorobenzenesulfonaMide, 97% is also utilized in the synthesis of other fine chemicals, where its reactivity and purity are essential for producing high-quality specialty chemicals for various applications.
Used in Dye and Pigment Production:
N-Benzyl-4-chlorobenzenesulfonamide, 97% serves as an important intermediate in the production of dyes and pigments, where its chemical properties are leveraged to create a wide range of colorants for different industries.
Overall, N-Benzyl-4-chlorobenzenesulfonamide, 97% is valued for its versatility and efficacy in chemical processes across multiple industries, including pharmaceuticals, agrochemicals, fine chemicals, and dye and pigment manufacturing.

InChI:InChI=1/C13H12ClNO2S/c14-12-6-8-13(9-7-12)18(16,17)15-10-11-4-2-1-3-5-11/h1-9,15H,10H2

Upstream product

• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 100-46-9 benzylamine 
• 2437-33-4 4-chlorobenzolsulfonsaeure-phenylester 
• 26971-85-7 p-Nitrophenyl p-chlorobenzenesulphonate 
• 80-33-1 chlorofensone 
• 37100-89-3 4-chloro-benzenesulfonic acid p-tolyl ester 
• 108-88-3 toluene 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 100-51-6 benzyl alcohol 
• 98-64-6 4-Chlorobenzenesulfonamide 
• 873-76-7 para-Chlorobenzyl alcohol 
• 973-63-7 2,4-dinitrophenyl 4-chlorobenzenesulfonate 

Downstream Products

• 52001-78-2 2-chloroethyl N-(p-chlorobenzenesulfonyl) N-benzyl carbamate 
• 51920-62-8 Isopropyl N-(p-chlorobenzenesulfonyl) N-benzyl carbamate 
• 276695-40-0 N-benzyl-N-[(4-chlorophenyl)sulfonyl]glycine 
• 333358-73-9 N-benzyl-N-[(4-chlorophenyl)sulfonyl]glycine methyl ester 
• 1392847-68-5 C₇₃H₁₀ClNO₂S 

Relevant articles and documents

Evidence for an Isocyanate Formation in the Alkaline Hydrolysis of N1-Alkyl Derivatives of Chlorpropamide, Inhibitors of Aldehyde Dehydrogenase

Trapping of a propyl isocyanate intermediate and entropies of activation data are consistent with an elimination-addition mechanism AxhDH + DN (E1cB) for the hydrolysis of 1-alkyl-1--3-n-propylurea, the N1-alkyl derivatives of chlorpropamide, inhibitors of aldehyde dehydrogenase.

Rhodium-catalyzed aerobic N-alkylation of sulfonamides with alcohols

By using the famous Wilkinson's catalyst, N-alkylation of sulfonamides can be easily realized under mild aerobic conditions by using alcohols as the alkylating reagent, giving monoalkylated sulfonamides in high yields and selectivities with water produced as the only byproduct. This advantageous aerobic method is potentially general in substrate scope that it can also be applied to other amides, amines and alcohols.

Triflic acid mediated functionalization of α-hydroxyphosphonates: Route for sulfonamide phosphonates

An operationally simple synthetic method for (±)-α-aryl/ methylsulfonamidomethylphosphonates and new (±)-γ-aryl/methyl sulfonamidomethylvinylphosphonates has been developed through straightforward reactions of (±)-α-hydroxyphosphonates with sulfonamides in the presence of triflic acid (TfOH) at room temperature in a vessel open to air. For γ-dimethylallylhydroxyphosphonate, the (E)-1,3-butadienylphosphonate was formed quantitatively using TfOH while FeCl3 afforded the expected product in moderate yield unpredictably. The favourable sulfonoamidation of benzyl alcohol is also observed when TfOH was used for α- hydroxyphosphonates having a benzyloxy group. The Royal Society of Chemistry 2013.

Discovery of N-amido-phenylsulfonamide derivatives as novel microsomal prostaglandin E2 synthase-1 (mPGES-1) inhibitors

Our previous research showed that N-carboxy-phenylsulfonyl hydrazide (scaffold A) could reduce LPS-stimulated PGE2 levels in RAW 264.7 macrophage cells by an inhibition of mPGES-1 enzyme. However, a number of scaffold A derivatives showed the drawbacks such as the formation of regioisomers and poor liver metabolic stability. In order to overcome these synthetic and metabolic problems, therefore, we decided to replace N-carboxy-phenylsulfonyl hydrazide (scaffold A) with N-carboxy-phenylsulfonamide (scaffold B) or N-amido-phenylsulfonamide frameworks (scaffold C) as a bioisosteric replacement. Among them, MPO-0186 (scaffold C) inhibited the production of PGE2 (IC50: 0.24 μM) in A549 cells via inhibition of mPGES-1 (IC50: 0.49 μM in a cell-free assay) and was found to be approximately 9- and 8-fold more potent than MK-886 as a reference inhibitor, respectively. A molecular docking study theoretically suggests that MPO-0186 could inhibit PGE2 production by blocking the PGH2 binding site of mPGES-1 enzyme. Furthermore, MPO-0186 demonstrated good liver metabolic stability and no significant inhibition observed in clinically relevant CYP isoforms except CYP2C19. This result provides a potential starting point for the development of selective and potent mPGES-1 inhibitor with a novel scaffold.

Method for synthesizing N-alkyl sulfonamide in water

The invention discloses a method for synthesizing N-alkyl sulfonamide in water, in particular to a method for synthesizing an N-alkyl sulfonamide derivative from a sulfonamide derivative and alcohol,and a water-soluble iridium complex is adopted to catalyze the reaction of N-alkyl sulfonamide. Compared with the previous synthesis method, the method has the advantages that a reaction equivalent substrate is used in the reaction process, so that raw material waste is avoided; weak base is used, and reaction conditions are mild; non-toxic and harmless pure water is used as a solvent in the reaction, only water is generated as a by-product, the atom reaction economy is high, and the requirement of green chemistry is met.

The: N -alkylation of sulfonamides with alcohols in water catalyzed by a water-soluble metal-ligand bifunctional iridium complex [Cp?Ir(biimH2)(H2O)][OTf]2

The iridium complex [Cp?Ir(biimH2)(H2O)][OTf]2 (Cp? = η5-pentamethylcyclopentadienyl, biimH2 = 2,2′-biimidazole) was synthesized and developed as a new-type of water-soluble metal-ligand bifunctional catalyst for the N-alkylation of poorly nucleophilic sulfonamides with alcohols in water. In the presence of catalyst (1 mol%) and Cs2CO3 (0.1 equiv.), a series of desirable products was obtained in 74-91% yields under microwave irradiation. Mechanistic experiments revealed that the presence of NH units in the imidazole ligand is crucially important for the catalytic activity of the iridium complex. Notably, this research would facilitate the process of water-soluble metal-ligand bifunctional catalysis for the hydrogen autotransfer process.

Method for catalytic synthesis of N-benzyl benzene sulfonamide compounds by boric acid/oxalic acid catalytic system under microwave radiation

The invention discloses a method for catalytic synthesis of N-benzyl benzene sulfonamide compounds by a boric acid/oxalic acid catalytic system under microwave radiation. The method includes: adoptingbenzyl alcohol and derivatives thereof and benzene sulfonamide derivatives as raw materials, adopting the boric acid/oxalic acid system as a catalyst, and adopting fluorobenzene as a solvent; performing reaction in a microwave reactor under certain temperature and power conditions, performing vacuum concentration after reaction for a period of time, and subjecting a product to column chromatographic purification to realize efficient catalytic preparation of the N-benzyl benzene sulfonamide compounds. Compared with the prior art, the method has advantages of evidently higher reaction speed than that of conventional heating, mild reaction conditions, simplicity in operation, high yield, safety, low cost and environmental friendliness.

Nondirected, cu-catalyzed sp3 C-H aminations with hydroxylamine-based amination reagents: Catalytic and mechanistic studies

This work demonstrates the use of hydroxylamine-based amination reagents RSO2NH-OAc for the nondirected, Cu-catalyzed amination of benzylic C-H bonds. The amination reagents can be prepared on a gram scale, are benchtop stable, and provide benzylic C-H amination products with up to 86% yield. Mechanistic studies of the established reactivity with toluene as substrate reveal a ligand-promoted, Cu-catalyzed mechanism proceeding through Ph-CH2(NTsOAc) as a major intermediate. Stoichiometric reactivity of Ph-CH2(NTsOAc) to produce Ph-CH2-NHTs suggests a two-cycle, radical pathway for C-H amination, in which the decomposition of the employed diimine ligands plays an important role.

Nickel-catalyzed product-controllable amidation and imidation of sp3 C-H bonds in substituted toluenes with sulfonamides

A nickel-catalyzed product-controllable imidation and amidation of sp3 C-H bonds in substituted toluenes with sulfonamides were developed. Based on the change of the reaction time and atmosphere from N2 to O2, this reaction proceeded in high yields and excellent selectivity under different conditions. Mechanistic details were also described.

Direct Alkylation of Amines with Alcohols Catalyzed by Base

A base-catalyzed/promoted transition-metal-free direct alkylation of amines with alcohols has been developed, giving the desired amines in generally high yields from either aromatic or aliphatic alcohols. On the basis of the 1H NMR and in situ IR (React-IR) monitoring experiments, isotope-labeling experiments, as well as control experiments, a novel "hemiaminal" model is proposed to understand the mechanism, which explains the formation of the "extra" aldehyde in the reaction.