58202-83-8

Basic information

• Product Name: Benzamide, 4-(acetylamino)-
• Synonyms: 4-Acetamino-benzamid;TYZ;p-acetamido-benzamide;Benzamide,4-acetamido;4-acetylamino-benzoic acid amide;Benzamide,4-acetylamino;4-Acetylamino-benzoesaeure-amid;4-acetylamino-benzamide
• CAS NO: 58202-83-8
• Molecular Formula: C9H10N2O2
• Molecular Weight: 178.191
• Mol File: 58202-83-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzamide, 4-(acetylamino)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, 4-(acetylamino)-(58202-83-8)
• EPA Substance Registry System: Benzamide, 4-(acetylamino)-(58202-83-8)

Safety Data

• Hazardous Substances Data: 58202-83-8(Hazardous Substances Data)

Upstream product

• 35704-19-9 N-(4-cyanophenyl)acetamide 
• 122-85-0 para-acetamidobenzaldehyde 
• 103-88-8 4-bromoacetanilide 
• 16375-88-5 N-(4-hydroxymethylphenyl)acetamide 

Downstream Products

• 94-09-7 p-aminoethylbenzoate 
• 619-45-4 4-methoxycarbonyl aniline 
• 35704-19-9 N-(4-cyanophenyl)acetamide 

Relevant articles and documents

Nitrogen Atom Transfer Catalysis by Metallonitrene C?H Insertion: Photocatalytic Amidation of Aldehydes

C?H amination and amidation by catalytic nitrene transfer are well-established and typically proceed via electrophilic attack of nitrenoid intermediates. In contrast, the insertion of (formal) terminal nitride ligands into C?H bonds is much less developed and catalytic nitrogen atom transfer remains unknown. We here report the synthesis of a formal terminal nitride complex of palladium. Photocrystallographic, magnetic, and computational characterization support the assignment as an authentic metallonitrene (Pd?N) with a diradical nitrogen ligand that is singly bonded to PdII. Despite the subvalent nitrene character, selective C?H insertion with aldehydes follows nucleophilic selectivity. Transamidation of the benzamide product is enabled by reaction with N3SiMe3. Based on these results, a photocatalytic protocol for aldehyde C?H trimethylsilylamidation was developed that exhibits inverted, nucleophilic selectivity as compared to typical nitrene transfer catalysis. This first example of catalytic C?H nitrogen atom transfer offers facile access to primary amides after deprotection.

A general and practical oxidation of alcohols to primary amides under metal-free conditions

A general procedure for oxidation of both benzyl alcohols and alkyl alcohols to primary amides under catalyst free conditions has been developed. 34 examples of primary amides were produced from their corresponding alcohols in moderate to excellent yields. This is a practical procedure for primary amides synthesis; water and tert-butanol are the only by-products. A commercial drug, Piracetam, was prepared in one step with 73% yield as well.