22184-93-6

Basic information

• Product Name: N-(2-hydroxyethyl)-m-nitrobenzenesulphonamide
• Synonyms: N-(2-hydroxyethyl)-m-nitrobenzenesulphonamide;N-(2-Hydroxyethyl)-m-nitrobenzenesulfonamide;N-(2-Hydroxyethyl)-3-nitrobenzenesulfonamide;Benzenesulfonamide, N-(2-hydroxyethyl)-3-nitro-;Einecs 244-823-5;N-Hydroxyethyl-3-nitrobenzenesulfonamide
• CAS NO: 22184-93-6
• Molecular Formula: C₈H₁₀N₂O₅S
• Molecular Weight: 246.2404
• EINECS: 244-823-5
• Mol File: 22184-93-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 452.9°Cat760mmHg
• Flash Point: 227.7°C
• Appearance: /
• Density: 1.484g/cm³
• Vapor Pressure: 5.41E-09mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: N-(2-hydroxyethyl)-m-nitrobenzenesulphonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-hydroxyethyl)-m-nitrobenzenesulphonamide(22184-93-6)
• EPA Substance Registry System: N-(2-hydroxyethyl)-m-nitrobenzenesulphonamide(22184-93-6)

Safety Data

• Hazardous Substances Data: 22184-93-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H10N2O5S/c11-5-4-9-16(14,15)8-3-1-2-7(6-8)10(12)13/h1-3,6,9,11H,4-5H2

Upstream product

• 141-43-5 ethanolamine 
• 121-51-7 3-nitrobenzenesulphonyl chloride 

Downstream Products

• 1370451-35-6 1-[2-(3-nitrophenylsulfonylamino)ethyl]-4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane 
• 1370451-41-4 1-[2-(3-aminophenylsulfonylamino)ethyl]-4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane 
• 99055-45-5 1-(3-nitro-benzenesulfonyl)-aziridine 
• 436095-41-9 3-amino-N-(2-hydroxyethyl)-benzenesulphonamide 
• 51983-28-9 3-nitro-benzenesulfonic acid-(2-chloro-ethylamide) 

Relevant articles and documents

Development of hypoxia-sensitive Gd3+-based MRI contrast agents

Hypoxia occurs in various diseases, including cancer, ischemia, and acute and chronic vascular diseases. Here we describe the design and synthesis of the first hypoxia-sensitive MRI contrast agents, SAGds. SAGds showed a pH-dependent r1 relaxivity change associated with intramolecular chelation of the nitrogen atom of the sulfonamide moiety to the Gd3+ center. There was a correlation between the pKa of the r1 relaxivity change and the sum of the Hammett σ constants of substituents on the aromatic ring. Among the synthesized compounds, 4NO22MeOSAGd was selectively reduced to the amine by rat liver microsomes under hypoxic conditions, resulting in a 1.8-fold increment of the r1 relaxivity owing to the change in pKa of the arylsulfonamide moiety. This enhancement of the r 1 relaxivity could be clearly detected in T1-weighted MR images. Thus, 4NO22MeOSAGd is a 'smart' MRI contrast agent for the detection of hypoxia under physiological conditions.