53865-58-0

Basic information

• Product Name: methyl 4-[(phenylcarbamoyl)amino]benzoate
• Synonyms: benzoic acid, 4-[[(phenylamino)carbonyl]amino]-, methyl ester; Methyl 4-[(phenylcarbamoyl)amino]benzoate
• CAS NO: 53865-58-0
• Molecular Formula: C₁₅H₁₄N₂O₃
• Molecular Weight: 270.2833
• Mol File: 53865-58-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 338.7°C at 760 mmHg
• Flash Point: 158.6°C
• Density: 1.3g/cm³
• Vapor Pressure: 9.66E-05mmHg at 25°C
• Refractive Index: 1.661
• CAS DataBase Reference: methyl 4-[(phenylcarbamoyl)amino]benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-[(phenylcarbamoyl)amino]benzoate(53865-58-0)
• EPA Substance Registry System: methyl 4-[(phenylcarbamoyl)amino]benzoate(53865-58-0)

Safety Data

• Hazardous Substances Data: 53865-58-0(Hazardous Substances Data)

Upstream product

• 98-95-3 nitrobenzene 
• 1384477-13-7 methyl 4-[(1H-imidazol-1-ylcarbonyl)amino]benzoate 
• 62-53-3 aniline 
• 103-71-9 phenyl isocyanate 
• 619-45-4 4-methoxycarbonyl aniline 

Relevant articles and documents

Structure-activity relationship and mechanistic studies for a series of cinnamyl hydroxamate histone deacetylase inhibitors

Histone deacetylases (HDACs) are a family of enzymes that modulate the acetylation status histones and non-histone proteins. Histone deacetylase inhibitors (HDACis) have emerged as an alternative therapeutic approach for the treatment of several malignanc

Synthesis of unsymmetrical biaryl ureas from N-carbamoylimidazoles: Kinetics and application

N-Carbamoylimidazoles dissociate in solution to yield imidazole and an isocyanate that may be reacted with another aryl amine to form an unsymmetrical biaryl urea. This paper investigates the reaction kinetics and the influence of electron withdrawing/donating substituents on the reaction of N-carbamoylimidazoles with aniline. The overall reaction mechanism involves two zwitterionic intermediates, formed during dissociation and upon reaction of the liberated isocyanate with aniline. The rate limiting step for the reaction is a base catalysed proton transfer from the second zwitterionic intermediate. Although electron withdrawing substituents on the aryl group hinder dissociation, they significantly increase reaction rates compared to compounds bearing electron donating substituents. The imidazole liberated upon dissociation catalyses the rate determining step so that reactions of dissociated N-carbamoylimidazoles proceed more rapidly than those involving only isocyanates. In addition, the imidazole eliminates the need for anhydrous reaction conditions. The N-carbamoylimidazole methodology was demonstrated by preparing sorafenib, a biaryl urea kinase inhibitor, in good yield and excellent purity.