3989-43-3

Basic information

• Product Name: N,N-DIPHENYL-METHANESULFONAMIDE
• Synonyms: N,N-DIPHENYL-METHANESULFONAMIDE
• CAS NO: 3989-43-3
• Molecular Formula: C₁₃H₁₃NO₂S
• Molecular Weight: 247.31282
• Mol File: 3989-43-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 116.5-117.0 °C(Solv: methanol (67-56-1))
• Boiling Point: 380.4 °C at 760 mmHg
• Flash Point: 183.8 °C
• Appearance: /
• Density: 1.267 g/cm³
• Vapor Pressure: 5.47E-06mmHg at 25°C
• Refractive Index: 1.623
• PKA: -6.41±0.50(Predicted)
• CAS DataBase Reference: N,N-DIPHENYL-METHANESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIPHENYL-METHANESULFONAMIDE(3989-43-3)
• EPA Substance Registry System: N,N-DIPHENYL-METHANESULFONAMIDE(3989-43-3)

Safety Data

• Hazardous Substances Data: 3989-43-3(Hazardous Substances Data)

Usage

General Description

N,N-Diphenyl-methanesulfonamide is a chemical compound that belongs to the class of sulfonamides. It is commonly used as an intermediate in the synthesis of pharmaceuticals and pesticides. This white crystalline solid is insoluble in water but soluble in organic solvents. It is known for its ability to act as a carbonic anhydrase inhibitor, which makes it useful in the treatment of glaucoma and other conditions related to increased intraocular pressure. It is also used as a catalyst in various organic reactions and as a stabilizer in plastic materials. Additionally, it has potential applications in the field of organic electronics due to its high thermal stability and electron-transport properties.

InChI:InChI=1/C13H13NO2S/c1-17(15,16)14(12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11H,1H3

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 122-39-4 diphenylamine 
• 3144-09-0 methanesulfonamide 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 1197-22-4 N-phenylmethanesulfonamide 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 98-80-6 phenylboronic acid 

Downstream Products

• 122-39-4 diphenylamine 

Relevant articles and documents

Mechanistic Insight Enables Practical, Scalable, Room Temperature Chan-Lam N-Arylation of N-Aryl Sulfonamides

Sulfonamides are profoundly important in pharmaceutical design. C-N cross-coupling of sulfonamides is an effective method for fragment coupling and structure-activity relationship (SAR) mining. However, cross-coupling of the important N-arylsulfonamide pharmacophore has been notably unsuccessful. Here, we present a solution to this problem via oxidative Cu-catalysis (Chan-Lam cross-coupling). Mechanistic insight has allowed the discovery and refinement of an effective cationic Cu catalyst to facilitate the practical and scalable Chan-Lam N-arylation of primary and secondary N-arylsulfonamides at room temperature. We also demonstrate utility in the large scale synthesis of a key intermediate to a clinical hepatitis C virus treatment.

Facile N-Arylation of Amines and Sulfonamides

(Matrix presented) A facile, transition-metal-free N-arylation procedure for amines and sulfonamides has been developed, which affords good to excellent yields of arylated products under very mild reaction conditions. A methoxy-substituted aryl triflate affords N-arylated products in high yields with excellent regioselectivity. This chemistry tolerates a variety of functional groups.

On the mechanism of sulfonamide cleavage by arene anion radicals.

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