587-14-4

Basic information

• Product Name: N,N'-Diphenylsulfamide
• Synonyms: N,N'-(Sulfonyl)bis(benzenamine);N,N'-Diphenylsulfamide;Sulfanilide
• CAS NO: 587-14-4
• Molecular Formula: C₁₂H₁₂N₂O₂S
• Molecular Weight: 248.3
• Mol File: 587-14-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 114 °C
• Boiling Point: 417.2°C at 760 mmHg
• Flash Point: 206.1°C
• Appearance: /
• Density: 1.362g/cm³
• Vapor Pressure: 3.61E-07mmHg at 25°C
• Refractive Index: 1.666
• PKA: 5.66±0.48(Predicted)
• CAS DataBase Reference: N,N'-Diphenylsulfamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Diphenylsulfamide(587-14-4)
• EPA Substance Registry System: N,N'-Diphenylsulfamide(587-14-4)

Safety Data

• Hazardous Substances Data: 587-14-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H12N2O2S/c13-17(15,16)14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,13,15,16)

Upstream product

• 87708-16-5 N-phenyl-2-oxooxazolidine-3-sulfonamide 
• 62-53-3 aniline 
• 106-50-3 1,4-phenylenediamine 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 
• 13449-19-9 N-Phenylsulfamoylazid 
• 76167-37-8 N-(chlorosulfonyl)benzanilide 
• 63489-51-0 acetyl-phenyl-sulfamoyl chloride 
• 858798-56-8 formyl-phenyl-sulfamoyl chloride 

Downstream Products

• 103-84-4 Acetanilid 
• 2364-50-3 isovaleranilide 
• 621-06-7 2,N-diphenylacetamide 
• 93-98-1 N-phenyl benzoyl amide 
• 102127-64-0 4-n-butyl-2,6-diphenyl-1,2,6-thiadiazin-3,5-(2H,6H)-dione 1,1-dioxide 
• 54767-78-1 N,N'-dimethyl-N,N'-diphenyl-sulfamide 
• 6833-13-2 2-chlorobenzanilide 
• 6832-98-0 palmitanilide 
• 2243-73-4 5-nitrobenzanilide 
• 620-71-3 N-(phenyl)-2-methylacetamide 
• 29824-70-2 N,N'-diacetyl-N,N'-diphenyl-sulfamide 
• 620-81-5 N,N'-Diphenyloxamid 
• 95196-99-9 N,N’-bis(4-bromophenyl)sulfamide 
• 71764-61-9 N,N'N-Trisphenyl-1,3,5-benzenetricarbonamide 

Relevant articles and documents

Electrochemical synthesis of sulfamides

Herein we demonstrate the first electrochemical synthesis protocol of symmetrical sulfamides directly from anilines and SO2mediated by iodide. Sulfamides are an emerging functional group in drug design. Highlights are the direct use of SO2from a stock solution and no necessity of any supporting electrolyte. Overall, the reaction has been demonstrated for 15 examples with yields up to 93%.

Vicinal Diamination of Arenes with Domino Aryne Precursors

Vicinal diamination of domino aryne precursors was achieved with sulfamides. The reaction proceeds through a two-aryne pathway, accepting two N-nucleophiles at the 1,2-positions of an arene ring. Symmetrical and unsymmetrical diaminobenzenes were readily obtained.

Investigation of the acid-catalyzed hydrolysis and reaction mechanisms of N,N′-diarylsulfamides using various criteria

The mechanism of acid-catalyzed hydrolysis of a series of p-substituted N,N′-diarylsulfamides was investigated in aqueous mineral acid solutions. Rate profiles, reaction activation parameters, catalytic order of strong acids, solvent isotope effects, and analysis of the kinetic data by the excess acidity method suggest a change in the mechanism from A2 to A1. While the hydrolysis proceeds with an A2 mechanism in low acidity regions, an A1 mechanism takes place in high acid concentrations. Copyright