5471-90-9

Basic information

• Product Name: Benzenesulfonamide, N-(4-hydroxyphenyl)-
• Synonyms: Benzenesulfonamide, N-(4-hydroxyphenyl)-
• CAS NO: 5471-90-9
• Molecular Formula: C₁₂H₁₁NO₃S
• Molecular Weight: 249.28564
• Mol File: 5471-90-9.mol

Chemical Properties

• Melting Point: 156 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 443.2°Cat760mmHg
• Flash Point: 221.8°C
• Appearance: /
• Density: 1.408g/cm³
• Vapor Pressure: 1.82E-08mmHg at 25°C
• Refractive Index: 1.661
• PKA: 9.65±0.10(Predicted)
• CAS DataBase Reference: Benzenesulfonamide, N-(4-hydroxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, N-(4-hydroxyphenyl)-(5471-90-9)
• EPA Substance Registry System: Benzenesulfonamide, N-(4-hydroxyphenyl)-(5471-90-9)

Safety Data

• Hazardous Substances Data: 5471-90-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzenesulfonamide, N-(4-hydroxyphenyl)is used as an active pharmaceutical ingredient for the development of drugs targeting conditions such as glaucoma, epilepsy, and certain types of cancer. Its carbonic anhydrase inhibitory properties make it a promising candidate for treating these diseases by modulating the activity of the enzyme involved in various physiological processes.
Used in Dye Production:
In the dye industry, Benzenesulfonamide, N-(4-hydroxyphenyl)serves as a key intermediate in the synthesis of various dyes. Its unique chemical structure allows for the creation of a wide range of colors and properties, making it a valuable component in the production of dyes for different applications.
Used as a Precursor in Organic Synthesis:
Benzenesulfonamide, N-(4-hydroxyphenyl)is utilized as a precursor in the synthesis of other organic compounds. Its versatile chemical structure enables it to be a building block for the development of new molecules with potential applications in various fields, including pharmaceuticals, materials science, and agrochemicals.
Used as a Reagent in Biochemical Research:
In biochemical research, Benzenesulfonamide, N-(4-hydroxyphenyl)is employed as a reagent for studying enzyme activity, particularly carbonic anhydrase. Its ability to inhibit the enzyme provides researchers with a valuable tool for understanding the enzyme's function and its role in various biological processes. Additionally, it can be used to investigate the mechanisms of action of other compounds that target carbonic anhydrase, contributing to the advancement of scientific knowledge in this area.

InChI:InChI=1/C12H11NO3S/c14-11-8-6-10(7-9-11)13-17(15,16)12-4-2-1-3-5-12/h1-9,13-14H

Upstream product

• 123-30-8 4-amino-phenol 
• 98-09-9 benzenesulfonyl chloride 
• 1809-20-7 diisopropyl hydrogenphosphonate 
• 4056-56-8 N-(phenylsulfonyl)-1,4-benzoquinone monoimine 
• 868-85-9 Dimethyl phosphite 
• 368-43-4 phenylsulfonyl fluoride 
• 150081-90-6 Dimethyl <2-hydroxy-5-phenyl>phosphonate 

Downstream Products

• 94042-55-4 2,6-bis(1-pyrrolidinylmethyl)-4-benzenesulfonamidophenol 
• 488-48-2 tetrabromobenzoquinone 
• 62638-01-1 N-benzenesulfonyl-2,6-dibromo-1,4-benzoquinone imine 
• 68374-96-9 N-phenylsulfonyl-2,3,6-trichloro-1,4-benzoquinone monoimine 
• 68375-07-5 N-phenylsulfonyl-2,3,6-trichloro-4-aminophenol 
• 4056-56-8 N-(4-Oxo-cyclohexa-2,5-dienylidene)-benzenesulfonamide 
• 36942-34-4 2-nitro-4-phenylsulfonamidophenol 
• 4056-56-8 N-(phenylsulfonyl)-1,4-benzoquinone monoimine 
• 201993-42-2 N-(2,3,5,5,6-pentachloro-4-oxo-cyclohex-2-enylidene)-benzenesulfonamide 
• 330212-89-0 2,3,5,6-tetrachloro-4-phenylsulfonylaminophenol 
• 51767-43-2 N-phenylsulfonyl-2-chloro-4-aminophenol 
• 1056125-18-8 N-(4-nitrooxy-phenyl)-benzenesulfonamide 
• 51767-46-5 N-(3,5-dibromo-4-hydroxyphenyl)benzenesulfonamide 
• 1343489-19-9 C₁₈H₂₁N₃O₃S 

Relevant articles and documents

Sulfonamide Synthesis via Calcium Triflimide Activation of Sulfonyl Fluorides

A method using calcium triflimide [Ca(NTf2)2] as a Lewis acid to activate sulfonyl fluorides toward nucleophilic addition with amines is described. The reaction converts a wide array of sterically and electronically diverse sulfonyl fluorides and amines into the corresponding sulfonamides in good yield.

PROCESS FOR SYNTHESIZING KETO-BENZOFURAN DERIVATIVES

The invention relates to a process for synthesizing benzofuran derivatives, in particular dronedarone of formula (D), comprising a step of Friedel-Crafts acylation starting from a sulfonamido-benzofuran ester intermediate.

Synthesis of 5-substituted 2,3-dihydrobenzofurans in a one-pot oxidation/cyclization reaction

Variously substituted 2,3-dihydrobenzofurans have been synthesized according to a sequential one-pot oxidation/cyclization procedure between para-aminophenol derivatives and an azadiene.

The novel behaviour of dialkyl phosphites toward 1,4-benzoquinone monoimines

Diethyl phosphite 2a reacts with N- (phenylsulfonyl) - 1,4 - benzoquinone monoimine 1a to give 1,4-diethyl [(2-hydroxy-5-[(phenylsulfonyl) amino ] phenyl] [sphosphonate 3a, diethyl (1-hydroxy - 4- [ ( phenylsulfonyl ) imino ] -2,5-cyclohexadiene )] phosph

Reactions of Phosphites with 1,4-Benzoquinone Monoimines

Trimethyl phosphite (2a) reacts with N-(phenylsulfonyl)-1,4-benzoquinone monoimine (1a) to give the respective phosphonate 3c, phosphates 3d, 3e and the alkylated products 3a and 3b.The reaction of triethyl phosphite (2b) with the same quinone imine 1a yi

STRUCTURE OF PRODUCTS FROM THE REACTION OF N-ARYLSULFONYL-p-QUINONE IMINES WITH NAPHTHOLS

Evidence was obtained for the addition of 2-naphthols to N-arylsulfonyl-p-benzo(naphtho)quinone imines at position 1 and of 1-naphthols at position 2 with the formation of 2-hydroxyaryl-4-arylsulfonylaminophenols (or the corresponding 1-naphthols). 5-Phen

Synthesis and antiarrhythmic and parasympatholytic properties of substituted phenols. 3. Modifications to the linkage region (region 3)

As part of a continuing program of systematically modifying the structure of the class I antiarrhythmic drug changrolin, we synthesized 15 analogues in which the linkage between the two aromatic regions was altered. High antiarrhythmic activity and low parasympatholytic activity was found when the linkage region, designated region 3, contained a carbonyl moiety, including ketones, amides, and ureas. Secondary amides were superior to tertiary amides, while amide reversal resulted in no change in activities. One compound in this series, 2,6-bis(1-pyrrolidinyl-methyl)-4-benzamidophenol (ACC-9358), is undergoing preclinical evaluations.