5466-91-1

Basic information

• Product Name: N-(4-aminophenyl)benzenesulfonamide
• Synonyms: N-(4-aminophenyl)benzenesulfonamide
• CAS NO: 5466-91-1
• Molecular Formula: C₁₂H₁₂N₂O₂S
• Molecular Weight: 248.31
• Mol File: 5466-91-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 447.6°Cat760mmHg
• Flash Point: 224.5°C
• Appearance: /
• Density: 1.373g/cm³
• Vapor Pressure: 3.61E-13mmHg at 25°C
• Refractive Index: 1.669
• CAS DataBase Reference: N-(4-aminophenyl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-aminophenyl)benzenesulfonamide(5466-91-1)
• EPA Substance Registry System: N-(4-aminophenyl)benzenesulfonamide(5466-91-1)

Safety Data

• Hazardous Substances Data: 5466-91-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H21N5O3/c1-15-19(21(28)26(24-15)16-7-3-2-4-8-16)23-22-18-10-6-5-9-17(18)20(27)25-11-13-29-14-12-25/h2-10,22H,11-14H2,1H3/b23-19-

Upstream product

• 1829-81-8 N-(4-nitrophenyl)benzenesulfonamide 
• 142-04-1 aniline hydrochloride 
• 36071-24-6 4-benzenesulfonylamino-benzenediazonium-betaine 
• 98-10-2 benzenesulfonamide 
• 106-40-1 4-bromo-aniline 
• 100-01-6 4-nitro-aniline 
• 98-09-9 benzenesulfonyl chloride 
• 98-80-6 phenylboronic acid 
• 603-33-8 triphenylbismuthane 
• 106-50-3 1,4-phenylenediamine 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 27022-75-9 4'-acetamidobenzenesulfonanilide 

Downstream Products

• 5467-02-7 1-benzenesulfonylamino-4-pivaloylamino-benzene 
• 65645-66-1 N¹-phenylsulfonyl-N⁴-(2-nitrophenylsulfonyl)-1,4-phenylenediamine 
• 86785-39-9 4'-(bromoacetamido)benzenesulfonanilide 
• 132904-25-7 N-[4-(Benzo[b][1,8]phenanthrolin-7-ylamino)-phenyl]-benzenesulfonamide 
• 86785-43-5 2'-chloro-4'-(bromoacetamido)benzenesulfonanilide 
• 86785-32-2 2-chloro-N¹-(phenylsulfonyl)-N⁴-(bromoacetyl)benzoquinone diimine 
• 86785-28-6 N¹-(phenylsulfonyl)-N⁴-(bromoacetyl)benzoquinone diimine 
• 134284-42-7 N-(4-Benzenesulfonylamino-3-chloro-phenyl)-2-nitro-benzenesulfonamide 
• 134284-39-2 N¹-phenylsulfonyl-N⁴-(2-nitrophenylsulfonyl)-1,4-benzoquinone diimine 
• 132904-16-6 12H-benzo<1,8>phenanthrol-7-one 

Relevant articles and documents

N-(4-acetamidophenyl)-5-acetylfuran-2-carboxamide as a novel orally available diuretic that targets urea transporters with improved PD and PK properties

Urea transporters (UTs) have been identified as new targets for diuretics. Functional deletion of UTs led to urea-selective urinary concentrating defects with relative salt sparing. In our previous study, a UT inhibitor with a diarylamide scaffold, which is denoted as 11a, was demonstrated as the first orally available UT inhibitor. However, the oral bioavailability of 11a was only 4.38%, which obstructed its clinical application. In this work, by replacing the nitro group of 11a with an acetyl group, 25a was obtained. Compared with 11a, 25a showed a 10 times stronger inhibitory effect on UT-B (0.14 μM vs. 1.41 μM in rats, and 0.48 μM vs. 5.82 μM in mice) and a much higher inhibition rate on UT-A1. Moreover, the metabolic stability both in vitro and in vivo and the drug-like properties (permeability and solubility) of 25a were obviously improved compared with those of 11a. Moreover, the bioavailability of 25a was 15.18%, which was 3 times higher than that of 11a, thereby resulting in significant enhancement of the diuretic activities in rats and mice. 25a showed excellent potential for development as a promising clinical diuretic candidate for targeting UTs to treat diseases that require long-term usage of diuretics, such as hyponatremia.

Sequential C-S and S-N Coupling Approach to Sulfonamides

A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.

Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound

The invention belongs to the field of organic synthesis, and specifically discloses a method for coupling a nitroaromatic compound and a boric acid compound to synthesize a sulfonamide compound. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound comprises the steps that in an organic solvent, pyrosulfite is used as a source of SO2,and heating is carried out for a coupling reaction, and then after the post-treatment, the sulfonamide compound is obtained. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound is simple in operation, does not require nitrogen protection, and can be carried out under air. The nitroaromatic compound and the boric acid compound are abundant in source, relatively low in price, high in reaction yield, wide in applicability of a substrate and free in metal residual. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound can be used for synthesizing a series of sulfonamide compounds, and the synthesized compounds have wide application value in the fields of pesticidesand medicines.