24855-58-1

Basic information

• Product Name: 4-hydroxy-3-nitrobenzenesulphonamide
• Synonyms: 4-hydroxy-3-nitrobenzenesulphonamide;2-Nitro-4-sulfamide phenol;Benzenesulfonamide, 4-hydroxy-3-nitro-;Einecs 246-499-0
• CAS NO: 24855-58-1
• Molecular Formula: C₆H₆N₂O₅S
• Molecular Weight: 218.18724
• EINECS: 246-499-0
• Mol File: 24855-58-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 203-206.5 °C
• Boiling Point: 419.7°C at 760 mmHg
• Flash Point: 207.6°C
• Appearance: /
• Density: 1.695g/cm³
• Vapor Pressure: 1.22E-07mmHg at 25°C
• Refractive Index: 1.646
• PKA: 4.85±0.14(Predicted)
• CAS DataBase Reference: 4-hydroxy-3-nitrobenzenesulphonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-3-nitrobenzenesulphonamide(24855-58-1)
• EPA Substance Registry System: 4-hydroxy-3-nitrobenzenesulphonamide(24855-58-1)

Safety Data

• Hazardous Substances Data: 24855-58-1(Hazardous Substances Data)

Usage

General Description

4-hydroxy-3-nitrobenzenesulphonamide, also known as Nifursol, is a chemical compound with the molecular formula C6H6N2O5S. It is a sulfonamide derivative with both hydroxy and nitro groups attached to the benzene ring. Nifursol has antimicrobial properties and has been used as an antiprotozoal and antibacterial agent in veterinary medicine, particularly in the treatment of coccidiosis in poultry. The compound is yellow in color and slightly soluble in water, and it is primarily used as a veterinary drug to prevent and treat parasitic infections in animals. However, it is important to note that Nifursol is banned for use in food-producing animals in the European Union due to concerns about its potential adverse effects on human health.

InChI:InChI=1/C6H6N2O5S/c7-14(12,13)4-1-2-6(9)5(3-4)8(10)11/h1-3,9H,(H2,7,12,13)

Upstream product

• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 39234-94-1 4-acetylamino-3-nitro-benzenesulfonic acid amide 
• 16761-19-6 4-acetylamino-3-nitro-benzenesulphonyl chloride 
• 2360-19-2 4-amino-3-nitrobenzenesulfonamide 
• 1576-43-8 4-hydroxybenzenesulphonamide 

Downstream Products

• 1228782-61-3 4-(3-(dimethylamino)propoxy)-3-nitrobenzenesulfonamide 
• 91559-86-3 6,6'-Dihydroxy-3,3'-disulfamoyl-diphenyl-disulfid 
• 90090-44-1 4-Methoxy-3-methylmercapto-benzolsulfonsaeure-amid 
• 88393-80-0 4-Methoxy-3-mercapto-benzolsulfonsaeure-amid 
• 98-32-8 3-amino-4-hydroxybenzenesulfonamide 

Relevant articles and documents

Appraisal of anti-protozoan activity of nitroaromatic benzenesulfonamides inhibiting carbonic anhydrases from Trypanosoma cruzi and Leishmania donovani

Chagas disease and leishmaniasis are neglected tropical disorders caused by the protozoans Trypanosoma cruzi and Leishmania spp. Carbonic anhydrases (CAs, EC 4.2.1.1) from these protozoans (α-TcCA and β-LdcCA) have been validated as promising targets for chemotherapic interventions. Many anti-protozoan agents, such as nitroimidazoles, nifurtimox, and benznidazole possess a nitro aromatic group in their structure which is crucial for their activity. As a continuation of our previous work on N-nitrosulfonamides as anti-protozoan agents, we investigated benzenesulfonamides bearing a nitro aromatic moiety against TcCA and LdcCA, observing selective inhibitions over human off-target CAs. Selected derivatives were assessed in vitro in different developmental stages of T. cruzi and Leishmania spp. A lack of significant growth inhibition has been found, which has been connected to the low permeability of this class of derivatives through cell membranes. Further strategies necessarily need to be designed for targeting Chagas disease and leishmaniasis with nitro-containing CA inhibitors.