5260-04-8

Basic information

• Product Name: N,N'-bis[4-(dimethylamino)phenyl]urea
• Synonyms: N,N'-bis[4-(dimethylamino)phenyl]urea
• CAS NO: 5260-04-8
• Molecular Weight: 298.388
• Mol File: 5260-04-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: N,N'-bis[4-(dimethylamino)phenyl]urea(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-bis[4-(dimethylamino)phenyl]urea(5260-04-8)
• EPA Substance Registry System: N,N'-bis[4-(dimethylamino)phenyl]urea(5260-04-8)

Safety Data

• Hazardous Substances Data: 5260-04-8(Hazardous Substances Data)

Upstream product

• 110-86-1 pyridine 
• 110-94-1 1,5-pentanedioic acid 
• 738-65-8 bis-(4-dimethylamino-phenyl)-carbodiimide 
• 71-43-2 benzene 
• 110-15-6 succinic acid 
• 67-56-1 methanol 
• 855181-09-8 N,N'-bis-(4-dimethylamino-phenyl)-N-trichloroacetyl-urea 
• 64-18-6 formic acid 
• 60-29-7 diethyl ether 
• 124-04-9 Adipic acid 
• 141-82-2 malonic acid 
• 16315-59-6 N,N-dimethylaminophenyl isocyanate 
• 123-76-2 levulinic acid 
• 7732-18-5 water 

Downstream Products

• 26271-84-1 hexa-N-methyl-4,4'-ureylene-di-anilinium; bis-dimethyl sulfate 

Relevant articles and documents

Hydrosilane-Assisted Synthesis of Urea Derivatives from CO2and Amines

A methodology employing CO2, amines, and phenylsilane was discussed to access aryl- or alkyl-substituted urea derivatives. This procedure was characterized by adopting hydrosilane to promote the formation of ureas directly, without the need to prepare silylamines in advance. Control reactions suggested that FeCl3 was a favorable additive for the generation of ureas, and this 1,5,7-triazabicyclo[4.4.0]dec-5-ene-catalyzed reaction might proceed through nucleophilic addition, silicon migration, and the subsequent formal substitution of silylcarbamate.

Synthesis of Urea Derivatives from CO2 and Silylamines

A series of thirty-three N,N′-diaryl, dialkyl, and alkyl-aryl ureas have been prepared in pyridine or toluene by reaction of silylamines with CO2. This protocol is shown to provide facile access to 13C-labeled ureas, as well as chiral and macrocyclic ureas. These reactions proceed through initial generation of the corresponding silylcarbamates, which subsequently react with silylamine under thermal conditions to afford the thermodynamically favored urea and disilyl ether.

Stoichiometric Reactions of CO2 and Indium-Silylamides and Catalytic Synthesis of Ureas

The indium compounds In(N(SiMe3)2)2Cl?THF (2) and In(N(SiMe3)2)Cl2?(THF)n (3) were shown to react with CO2 to give [(Me3Si)2N)InX(μ-OSiMe3)]2 (X=N(SiMe3)2 4, Cl 5). 0.05–2.0 mol % of the species 3 acts as a pre-catalyst for the conversion of aryl and alkyl silylamines under CO2 (2–3 atm) to give the corresponding ureas in 70–99 % yields. A proposed mechanism is supported by experimental and computational data.