73153-44-3

Basic information

• Product Name: N-(methylsulfonyl)-N-phenylbenzamide
• Synonyms: N-(methylsulfonyl)-N-phenylbenzamide
• CAS NO: 73153-44-3
• Molecular Weight: 275.328
• Mol File: 73153-44-3.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: N-(methylsulfonyl)-N-phenylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(methylsulfonyl)-N-phenylbenzamide(73153-44-3)
• EPA Substance Registry System: N-(methylsulfonyl)-N-phenylbenzamide(73153-44-3)

Safety Data

• Hazardous Substances Data: 73153-44-3(Hazardous Substances Data)

Upstream product

• 676-85-7 methylsulphinyl chloride 
• 304-88-1 N-phenylbenzohydroxamic acid 
• 73153-40-9 C₁₄H₁₃NO₃S 
• 100-46-9 benzylamine 
• 62-53-3 aniline 
• 98-88-4 benzoyl chloride 
• 124-63-0 methanesulfonyl chloride 
• 2902-69-4 2,2,2-trichloroacetophenone 
• 1197-22-4 N-phenylmethanesulfonamide 

Downstream Products

• 884-09-3 phenyl thiobenzoate 
• 55-21-0 benzamide 
• 613-37-6 4-methoxylbiphenyl 
• 582-78-5 N-(4-methylphenyl)benzamide 
• 4433-30-1 1-phenylundecan-1-one 
• 1754-49-0 diethyl phenylphosphonate 
• 954-16-5 2,4,6-Trimethylbenzophenon 
• 179113-89-4 (3,5-difluorophenyl)(phenyl)methanone 
• 4038-14-6 3,4-dimethoxybenzophenone 
• 345-69-7 3-fluorobenzophenone 
• 6136-67-0 3-methoxybenzophenone 
• 16780-82-8 2-benzoylbenzaldehyde 
• 20912-50-9 4-benzoylbenzaldehyde 
• 53689-84-2 4-acetylbenzophenone 

Relevant articles and documents

Thioesterification and Selenoesterification of Amides via Selective N-C Cleavage at Room Temperature: N-C(O) to S/Se-C(O) Interconversion

The direct nucleophilic addition to amides represents an attractive methodology in organic synthesis that tackles amidic resonance by ground-state destabilization. This approach has been recently accomplished with carbon, nitrogen and oxygen nucleophiles.

Sterically Hindered Ketones via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Amides by N-C(O) Activation

Herein, we report a new protocol for the synthesis of sterically hindered ketones that proceeds via palladium-catalyzed Suzuki-Miyaura cross-coupling of unconventional amide electrophiles by selective N-C(O) activation. Mechanistic studies demonstrate that steric bulk on the amide has a major impact, which is opposite to the traditional Suzuki-Miyaura cross-coupling of sterically hindered aryl halides. Structural and computational studies provide insight into ground-state distortion of sterically hindered amides and show that ortho-substitution alleviates the N-C(O) bond twist.

Decarbonylative Phosphorylation of Amides by Palladium and Nickel Catalysis: The Hirao Cross-Coupling of Amide Derivatives

Considering the ubiquity of organophosphorus compounds in organic synthesis, pharmaceutical discovery agrochemical crop protection and materials chemistry, new methods for their construction hold particular significance. A conventional method for the synthesis of C?P bonds involves cross-coupling of aryl halides and dialkyl phosphites (the Hirao reaction). We report a catalytic deamidative phosphorylation of a wide range of amides using a palladium or nickel catalyst giving aryl phosphonates in good to excellent yields. The present method tolerates a wide range of functional groups. The reaction constitutes the first example of a transition-metal-catalyzed generation of C?P bonds from amides. This redox-neutral protocol can be combined with site-selective conventional cross-coupling for the regioselective synthesis of potential pharmacophores. Mechanistic studies suggest an oxidative addition/transmetallation pathway. In light of the importance of amides and phosphonates as synthetic intermediates, we envision that this Pd and Ni-catalyzed C?P bond forming method will find broad application.