124772-05-0

Basic information

• Product Name: N-(4-HYDROXY-PHENYL)-4,N-DIMETHYL-BENZENESULFONAMIDE
• Synonyms: N-(4-hydroxyphenyl)-N,4-dimethylbenzenesulfonamide
• CAS NO: 124772-05-0
• Molecular Formula: C₁₄H₁₅NO₃S
• Molecular Weight: 277.3388
• Mol File: 124772-05-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 138 °C
• Boiling Point: 462.2 °C at 760 mmHg
• Flash Point: 233.3 °C
• Appearance: /
• Density: 1.309 g/cm³
• Vapor Pressure: 3.66E-09mmHg at 25°C
• Refractive Index: 1.625
• PKA: 9.34±0.15(Predicted)
• CAS DataBase Reference: N-(4-HYDROXY-PHENYL)-4,N-DIMETHYL-BENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-HYDROXY-PHENYL)-4,N-DIMETHYL-BENZENESULFONAMIDE(124772-05-0)
• EPA Substance Registry System: N-(4-HYDROXY-PHENYL)-4,N-DIMETHYL-BENZENESULFONAMIDE(124772-05-0)

Safety Data

• Hazardous Substances Data: 124772-05-0(Hazardous Substances Data)

Usage

General Description

N-(4-Hydroxy-phenyl)-4,N-dimethyl-benzenesulfonamide is a chemical compound with the molecular formula C14H15NO3S. It is a sulfonamide derivative, which is widely used in pharmaceutical research as a pharmacological inhibitor of carbonic anhydrases (CAs). N-(4-HYDROXY-PHENYL)-4,N-DIMETHYL-BENZENESULFONAMIDE has been studied for its potential therapeutic applications in the treatment of various medical conditions, including glaucoma, epilepsy, and cancer. It is known to exhibit inhibitory activity against various isoforms of carbonic anhydrase enzymes, making it a valuable tool for studying the physiological roles of these enzymes and developing novel therapeutic agents. Additionally, it has also been investigated for its potential anti-inflammatory and analgesic properties.

InChI:InChI=1/C14H15NO3S/c1-11-3-9-14(10-4-11)19(17,18)15(2)12-5-7-13(16)8-6-12/h3-10,16H,1-2H3

Upstream product

• 512-56-1 trimethyl phosphite 
• 1146-43-6 N-(4-hydroxyphenyl)-4-methylbenzenesulfonamide 
• 3899-93-2 4-aminophenyl-4-toluenesulfonic acid ester 
• 84573-28-4 4-{[(4-methylphenyl)sulfonyl]amino}phenyl 4-methylbenzenesulfonate 
• 123-30-8 4-amino-phenol 
• 51-72-9 4-(methylamino)phenol sulfate 
• 98-59-9 p-toluenesulfonyl chloride 
• 857005-19-7 toluene-4-sulfonic acid-[4-(2,4-dinitro-phenoxy)-anilide] 
• 2363-30-6 4-amino-2',4'-dinitrodiphenyl ether 
• 857005-17-5 toluene-4-sulfonic acid-[4-(2,4-dinitro-phenoxy)-N-methyl-anilide] 

Downstream Products

• 1091821-84-9 2-(4-{methyl[(4-methylphenyl)sulfonyl]amino} phenoxy)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)acetamide 
• 102319-75-5 N,N'-dimethyl-4,4'-pentanediyldioxy-di-aniline 
• 104623-15-6 1,5-bis-{4-[methyl-(toluene-4-sulfonyl)-amino]-phenoxy}-pentane 

Relevant articles and documents

A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.

O- and N-substituted derivatives of planetol as valuable bioactive compounds

The compounds bearing sulfamoyl and acetamoyl groups have been found to show various biological activities. In the present research work, a series of O- and N-substituted derivatives were synthesized, starting with planetol (1). First N-methyl-4-hydroxyanilinium sulfate (1; planetol or metol) was treated with different aryl sulfonyl chlorides (2a-i) using aq. sodium carbonate solution as reaction medium to yield N-substituted derivatives 3a-i. The electrophile, N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-bromoacetamide (5) was prepared by the reaction of 2,3-dihydro-1,4-benzodioxin-6-amine (4) and 2-bromoacetylbromide in a weak basic aqueous medium. The target O-substituted molecules 6a-i, were synthesized by gearing up the electrophile 5, with the molecules 3a-i, in a polar aprotic solvent using LiH as an activator. The proposed structures of all the synthesized molecules were corroborated by IR,1H NMR and EIMS spectral data. The in vitro enzyme inhibition and antibacterial studies rendered the synthesized molecules as better cholinesterase inhibitors and moderately better antibacterial agents. To explore the binding modes of the synthesized compounds, all of them were computationally docked against the active sites of acetyl cholinesterase (AChE), butyryl cholinesterase (BChE) and lipoxygenase (LOX). The compounds showed significant interactions and good correlation with the experimental data.