31220-71-0

Basic information

• Product Name: N-(HYDROXYMETHYL)-4-METHYLBENZAMIDE
• Synonyms: N-(HYDROXYMETHYL)-4-METHYLBENZAMIDE
• CAS NO: 31220-71-0
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• Mol File: 31220-71-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(HYDROXYMETHYL)-4-METHYLBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(HYDROXYMETHYL)-4-METHYLBENZAMIDE(31220-71-0)
• EPA Substance Registry System: N-(HYDROXYMETHYL)-4-METHYLBENZAMIDE(31220-71-0)

Safety Data

• Hazardous Substances Data: 31220-71-0(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 619-55-6 para-methylbenzamide 

Downstream Products

• 93415-05-5 N-(3,4-Dimethoxy-phenylsulfanylmethyl)-4-methyl-benzamide 
• 99-94-5 p-Toluic acid 
• 619-55-6 para-methylbenzamide 
• 91937-62-1 6,7-dimethoxy-2-(p-methylphenyl)-4H-1,3-benzothiazine 
• 91937-65-4 6,7-Dimethoxy-4-p-tolyl-2H-benzo[e][1,3]thiazine 
• 40478-22-6 N-{[Bis-(2-chloro-ethyl)-amino]-methyl}-4-methyl-benzamide 
• 67853-08-1 N-Chloromethyl-4-methyl-benzimidoyl chloride 

Relevant articles and documents

A convenient and clean synthesis of methylenebisamides and carbinolamides over zeolites in aqueous media

A simple, efficient and environmentally benign protocol for the synthesis of methylenebisamides and carbinolamides in high yields from aromatic amides and formaldehyde in the presence of heterogeneous catalysts (Hβ and NaY zeolites) using water as a solvent is demonstrated. Moreover, the catalyst is recyclable and can be reused without significant loss in its catalytic activity.

Rapid amidic hydrolysis: a competitive reaction pathway under basic conditions for N-(hydroxymethyl)benzamide derivatives bearing electron-donating groups

Studies of N-(hydroxymethyl)benzamide derivatives have concluded that the hydroxide-dependent reaction occurs via a specific-base catalyzed deprotonation of the hydroxyl group followed by rate-determining loss of the benzamidate and generation of the aldehyde. The 3-methyl, 4-methyl, and 4-methoxy-N-(hydroxymethyl)benzamide reaction mechanism deviates at higher [HO-] with amidic hydrolysis becoming competitive and having reaction half-lives of ～17 s, in 1 M KOH, I = 1.0 M (KCl), 25 °C. An intramolecular general-base catalyzed mechanism has been suggested for the amidic hydrolysis reaction.

Rate of formation of N-(hydroxymethyl)benzamide derivatives in water as a function of pH and their equilibrium constants

The third-order rate constants for the pH-dependent formation of the carbinolamides generated from the reaction of formaldehyde and benzamide, 4-chloro, 4-nitro, 4-methyl and 4-methoxybenzamide, are reported. The acid-catalyzed reaction was found to occur via rate-limiting proton transfer, whereas the hydroxide-dependent reaction occurred via a specific-base process. Coupling the rate constants for carbinolamide formation reported herein with the previously established rates for carbinolamide breakdown yielded equilibrium constants for the carbinolamides studied in water.