104542-78-1

Basic information

• Product Name: N,N'-bis(p-nitrobenzoyl)methanediamine
• Synonyms: N,N'-bis(p-nitrobenzoyl)methanediamine
• CAS NO: 104542-78-1
• Molecular Weight: 344.283
• Mol File: 104542-78-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: N,N'-bis(p-nitrobenzoyl)methanediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-bis(p-nitrobenzoyl)methanediamine(104542-78-1)
• EPA Substance Registry System: N,N'-bis(p-nitrobenzoyl)methanediamine(104542-78-1)

Safety Data

• Hazardous Substances Data: 104542-78-1(Hazardous Substances Data)

Upstream product

• 67-68-5 dimethyl sulfoxide 
• 619-72-7 4-nitrobenzonitrile 
• 33288-81-2 N,N'-(ethane?1,2?diyl)bis(4?nitrobenzamide) 
• 75-05-8 acetonitrile 
• 619-80-7 4-nitrobenzamide 
• 87576-94-1 trimethylsilylmethyl azide 
• 122-04-3 4-nitro-benzoyl chloride 
• 50-00-0 formaldehyd 
• 758-96-3 N,N-dimethyl-propanamide 

Relevant articles and documents

One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine

Symmetrical bisamides of ethylene diamine of type ArCONHCH2CH2NHCOAr undergo anodic C-C bond cleavage in acetonitrile-LiClO4 under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem-bisamides of type ArCONHCH2NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor products involve two symmetrical gem-bisamides of type ArCONHCH2NHCOAr and MeCONHCH2NHCOMe and fragmentation products (e.g., ArCONHCHO, ArCONH2, and ArCN).

Ammonium persulfate activated DMSO as a one-carbon synthon for the synthesis of methylenebisamides and other applications

Activation of DMSO to work as an economical and environmentally benign one-carbon synthon has been achieved by using a bench-top reagent ammonium persulfate for general and efficient access to symmetrical methylenebisamides from primary amides. This methodology was used to achieve a three-component Mannich reaction using acetophenone, saccharin and DMSO to furnish a β-amino ketone. It also provided a metal-free synthesis of thiadiazole and bis(phenyl)methane. Effectively, this method uses DMSO as a safer surrogate to formaldehyde. A mechanism for methylenebisamide formation involving radical intermediates has been proposed based on mechanistic studies.

Synthesis of methylenebisamides by TFA-promoted reactions of nitriles and DMSO

Under TFA promoted conditions, aryl and 2-pyridyl nitriles can react with DMSO, affording methylenebisamides in moderate to good yields. While the electron-donating groups give good yields, the electron-withdrawing groups provide lower yields.