82212-42-8

Basic information

• Product Name: Benzamide, N-(phenoxymethyl)-
• CAS NO: 82212-42-8
• Molecular Formula: C14H13NO2
• Molecular Weight: 227.263
• Mol File: 82212-42-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzamide, N-(phenoxymethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-(phenoxymethyl)-(82212-42-8)
• EPA Substance Registry System: Benzamide, N-(phenoxymethyl)-(82212-42-8)

Safety Data

• Hazardous Substances Data: 82212-42-8(Hazardous Substances Data)

Upstream product

• 78134-74-4 (benzoylaminomethyl)triethylammonium chloride 
• 108-95-2 phenol 
• 38792-42-6 N-(chloromethyl)benzamide 
• 6282-02-6 N-(hydroxymethyl)benzamide 
• 55-21-0 benzamide 
• 1019770-60-5 BF₄^(1-)*C₂₆H₂₃NOP⁽¹⁺⁾ 
• 495-69-2 Hippuric Acid 

Relevant articles and documents

Amidoalkylating properties of 1-(N -acylamino)alkyltriphenylphosphonium salts

Easily accessible 1-(N-acylamino)alkyltriphenylphosphonium salts react smoothly with nitrogen, sulfur, phosphorus and oxygen nucleophiles in the presence of (i-Pr)2EtN to give the expected α-amidoalkylation products, usually in good or very good yields. α-Amidoalkylation of dialkyl malonates or acetylacetates requires the application of a much stronger base (DBU) and gives the best results under the influence of microwave irradiation. α-Amidoalkylation of enamines was carried out successfully in the presence of (i-Pr)2EtN in a microwave reactor. 1-(N-Acylamino)alkyltriphenylphosphonium salts can be considered as new, convenient and effective α-amidoalkylation agents.

Mechanism of Hydrolysis of Benzamidomethyl Derivatives of Phenols and Its Implications for Prodrug Design

A series of O-benzamidomethyl derivatives of phenols was synthesized, and their rates of hydrolysis were investigated.The hydrolyses of the compounds follow pseudo-first-order kinetics resulting in quantitative and rapid regeneration of the phenol.The rates of hydrolysis were shown to be dependent on phenol nucleofugicity as well as the pKa of the amide.The mechanism of hydrolysis apparently involves as elimination of the phenol anion from the conjugate base of the amide (E1cB-like).