1576-48-3

Basic information

• Product Name: N-phenylnaphthalene-2-sulfonamide
• Synonyms: 2-naphthalenesulfonamide, N-phenyl-; 2-Naphthalenesulfonanilide; N-Phenylnaphthalene-2-sulfonamide
• CAS NO: 1576-48-3
• Molecular Formula: C₁₆H₁₃NO₂S
• Molecular Weight: 283.3449
• Mol File: 1576-48-3.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 474.5°C at 760 mmHg
• Flash Point: 240.8°C
• Density: 1.332g/cm³
• Vapor Pressure: 3.59E-09mmHg at 25°C
• Refractive Index: 1.692
• CAS DataBase Reference: N-phenylnaphthalene-2-sulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-phenylnaphthalene-2-sulfonamide(1576-48-3)
• EPA Substance Registry System: N-phenylnaphthalene-2-sulfonamide(1576-48-3)

Safety Data

• Hazardous Substances Data: 1576-48-3(Hazardous Substances Data)

Upstream product

• 62-53-3 aniline 
• 93-11-8 2-Naphthalenesulfonyl chloride 
• 32316-92-0 naphthalene-2-boronic acid 
• 98-95-3 nitrobenzene 
• 13407-52-8 2-naphthalenesulphonyl azide 
• 98-80-6 phenylboronic acid 
• 63735-42-2 sodium naphthalen-2-ylsulfinate 
• 1576-47-2 2-naphthalenesulphonamide 
• 873-55-2 sodium benzenesulfonate 
• 591-50-4 iodobenzene 

Downstream Products

• 542-11-0 aniline hydrobromide 
• 304694-54-0 ethyl 5-(naphthalene-2-sulfonamido)-2-phenylbenzofuran-3-carboxylate 
• 91-60-1 2-Naphthalenethiol 
• 106-47-8 4-chloro-aniline 

Relevant articles and documents

Preparation of acid-labile resins with halide linkers and their utility in solid phase organic synthesis

Mild and efficient preparation of acid-labile resins with displaceable halide linkers (3 and 4, X = Br and I) is described. These resins can be used in combinatorial organic synthesis of numerous drug-scaffold libraries. Their synthetic utility is exemplified by high yielding N-alkylations with structurally and electronically diverse sets of aliphatic and aromatic amines. Amongst the various resins modified and evaluated in this study, Wang resin derived bromo resin (3, X = Br) offers the best practical choice with respect to loading, stability, and chemical reactivity.

Copper-Catalyzed Aminoarylation of Alkenes via Aminyl Radical Addition and Aryl Migration

We describe a new strategy for aminoarylation of alkenes by copper-catalyzed smiles rearrangement using O-benzoylhydroxylamines as the amine reagent. This method affords various β-amino amide derivatives possessing a quaternary carbon center with wide functional group tolerance and high regioselectivity. The mechanistic studies indicate that the transformation can involve aminyl radical intermediates under acid-free condition.

Copper-catalyzed synthesis of sulfonamides from nitroarenes: Via the insertion of sulfur dioxide

Nitroarenes are used as the coupling partners in the preparation of sulfonamides via the insertion of sulfur dioxide. A three-component reaction of arylboronic acids, nitroarenes, and potassium metabisulfite under copper catalysis proceeds smoothly, giving rise to a range of sulfonamides in good to excellent yields with broad substrate scope. Various functional groups including hydroxyl, cyano, amino, and carbonyl are all tolerated. A plausible mechanism is proposed, showing that arylsulfinate is the intermediate and the copper-assisted interaction of the nitroarene and arylsulfinate is the key step. This approach is also extended to the late-stage modification of a currently marketed drug (flutamide).

A Versatile Synthesis of Vinyl-Substituted Heterocycles via Regio- And Enantioselective Pd-Catalyzed Tandem Allylic Substitution

We herein report a versatile, regio- and enantioselective palladium-catalyzed tandem allylic substitution powered by a chiral bisphosphorus ligand WingPhos with the palladium loading as low as 0.1 mol %, forming a series of chiral vinyl-substituted heterocycles, including tetrahydroquinoxalines, piperazines, dihydro-2H-benzo[b][1,4]-oxazines, and morpholines, in exellent ee's and yields. The protocol features readily available starting materials, mild reaction conditions, and a broad substrate scope. Mechanistic investigation supports a tandem allylic substitution process.