587-57-5

Basic information

• Product Name: N-[3,5-bis(trifluoromethyl)phenyl]-4-nitrobenzenesulfonamide
• Synonyms: benzenesulfonamide, N-[3,5-bis(trifluoromethyl)phenyl]-4-nitro-
• CAS NO: 587-57-5
• Molecular Formula: C₁₄H₈F₆N₂O₄S
• Molecular Weight: 414.2797
• Mol File: 587-57-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 424.2°C at 760 mmHg
• Flash Point: 210.3°C
• Density: 1.609g/cm³
• Vapor Pressure: 2.11E-07mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: N-[3,5-bis(trifluoromethyl)phenyl]-4-nitrobenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[3,5-bis(trifluoromethyl)phenyl]-4-nitrobenzenesulfonamide(587-57-5)
• EPA Substance Registry System: N-[3,5-bis(trifluoromethyl)phenyl]-4-nitrobenzenesulfonamide(587-57-5)

Safety Data

• Hazardous Substances Data: 587-57-5(Hazardous Substances Data)

Upstream product

• 328-74-5 3,5-Bis-(trifluoromethyl)aniline 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 

Downstream Products

• 404-02-4 NSC 56605-K 

Relevant articles and documents

Electron-withdrawing substituted benzenesulfonamides against the predominant community-associated methicillin-resistant Staphylococcus aureus strain USA300

A small focused chemical library constituted of sulfonamides was synthesized. These compounds were designed to lack the p-aminobenzene moiety typically found in sulfonamide antibiotics. Antimicrobial activities of these synthetic compounds were investigated against global predominant methicillin-resistant Staphylococcus aureus (MRSA) strain USA300 (SF8300) and control strains of Staphylococcus aureus (S. aureus) ATCC 25923 and ATCC 29213 using disk diffusion and microdilution assays. Based on susceptibility results, potent S. aureus and MRSA USA300 growth inhibitors such as N-[3,5- bis(trifluoromethyl)phenyl]-4-bromobenzenesulfonamide with minimum inhibitory concentration (MIC) as low as 5.6 μg/cm3 along with other effective sulfonamides were discovered. Structure-activity correlations revealed that these desamino-benzenesulfonamides required electron-withdrawing substituents to be effective inhibitors of bacterial pathogen growth. In addition, their ability to inhibit growth of S. aureus strains was retained even when bacterial folate synthetic intermediate, p-aminobenzoic acid (PABA), was supplemented, whereas PABA supplementation completely diminished the antibacterial activity of the known sulfa drug tested, sulfamethoxazole. The sulfa-resistant MRSA strain COL also showed great susceptibility to these desamino-benzenesulfonamides. These results imply a unique mechanism of growth inhibition by these potent desamino-benzenesulfonamides, different from the well-known folate pathway target of sulfonamide antibiotics.

Analgesic agents without gastric damage: Design and synthesis of structurally simple benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors

In order to create novel analgesic agents without gastric disturbance, structurally simple cyclooxygenase-1 (COX-1) inhibitors with a benzenesulfonanilide skeleton were designed and synthesized. As a result, compounds 11f and 15a, which possess a p-amino group on the benzenesulfonyl moiety and p-chloro group on the anilino moiety, showed COX-1-selective inhibition. Moreover compound 11f, which is the most potent compound in this study showed more potent analgesic activity than that of aspirin at 30 mg/kg by po. The anti-inflammatory activity and gastric damage, however, were very weak or not detectably different from aspirin. Since the structure of our COX-1 inhibitors are very simple, they may be useful as lead compounds for superior COX-1 inhibitors as analgesic agents without gastric disturbance.