735-57-9

Basic information

• Product Name: N-(4-Methyl-2-nitrophenyl)benzenesulfonamide
• Synonyms: N-(4-Methyl-2-nitrophenyl)benzenesulfonamide
• CAS NO: 735-57-9
• Molecular Formula: C₁₃H₁₂N₂O₄S
• Molecular Weight: 292.31038
• Mol File: 735-57-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 465.6°Cat760mmHg
• Flash Point: 235.4°C
• Appearance: /
• Density: 1.414g/cm³
• Vapor Pressure: 7.6E-09mmHg at 25°C
• Refractive Index: 1.641
• CAS DataBase Reference: N-(4-Methyl-2-nitrophenyl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Methyl-2-nitrophenyl)benzenesulfonamide(735-57-9)
• EPA Substance Registry System: N-(4-Methyl-2-nitrophenyl)benzenesulfonamide(735-57-9)

Safety Data

• Hazardous Substances Data: 735-57-9(Hazardous Substances Data)

Usage

General Description

N-(4-Methyl-2-nitrophenyl)benzenesulfonamide is a chemical compound with the molecular formula C13H12N2O4S. It is commonly used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. This chemical is a nitrophenyl derivative of benzenesulfonamide, and it has potential applications in the field of medicinal chemistry due to its structural properties. It is important to handle N-(4-Methyl-2-nitrophenyl)benzenesulfonamide with care, as it may have health and environmental hazards, and proper safety measures should be followed when working with this compound.

InChI:InChI=1/C13H12N2O4S/c1-10-7-8-12(13(9-10)15(16)17)14-20(18,19)11-5-3-2-4-6-11/h2-9,14H,1H3

Upstream product

• 6311-65-5 N-p-tolyl-benzenesulfonamide 
• 98-09-9 benzenesulfonyl chloride 
• 89-62-3 4-methyl-2-nitroaniline 
• 106-49-0 p-toluidine 

Downstream Products

• 81262-51-3 benzenesulfonic acid-(2-amino-4-methyl-anilide) 
• 81262-52-4 5-methyl-1-(phenylsulfonyl)benzotriazole 

Relevant articles and documents

Silver-Catalyzed Chemo- and Regioselective Nitration of Anilides

A new and efficient Ag-catalyzed method for the nitration of anilides by using sodium nitrite as a cheap and available NO2 source has been developed. This C–H functionalization reaction is ortho-selective, achieves moderate to high yields and shows excellent functional group tolerance. Furthermore, it provides a novel approach to ortho-nitrated anilides, which are very tricky to access with traditional methods.

Potent anti-prostate cancer agents derived from a novel androgen receptor down-regulating agent

The search for novel androgen receptor (AR) down-regulating agents by catalyst HipHop pharmacophore modeling led to the discovery of some lead molecules. Unexpectedly, the effect of these leads on human prostate cancer LNCaP cell viability did not correlate with the ability of the compounds to cause down-regulation of AR protein expression. Through rational synthetic optimization of the lead compound (BTB01434), we have discovered a series of novel substituted diaryl molecules as potent anti-prostate cancer agents. Some compounds (1-6) were shown to be extremely potent inhibitors of LNCaP cell viability with GI50 values in the nanomolar range (1.45-83 nM). The most potent compound (4-methylphenyl)[(4-methylphenyl)sulfonyl]amine (5) with a GI50 value of 1.45 nM is 27,000 times more potent than our lead compound BTB01434 (GI50 = 39.8 μM). In addition, some of the compounds exhibited modest anti-androgenic activities and one was also a potent inhibitor (GI50 = 850 nM) of PC-3 (AR-null) cell growth. A clear structure-activity relationship (SAR) has been established for activity against LNCaP cells, where potent molecules possess two substituted/unsubstituted aromatic rings connected through a sulfonamide linker. These novel compounds are strong candidates for development for the treatment of hormone-sensitive and importantly hormone-refractory prostate cancers in humans.