87623-47-0

Basic information

• Product Name: N-n-propyl-2-mercaptomethylbenzamide
• Synonyms: N-n-propyl-2-mercaptomethylbenzamide
• CAS NO: 87623-47-0
• Molecular Weight: 209.312
• Mol File: 87623-47-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-n-propyl-2-mercaptomethylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-n-propyl-2-mercaptomethylbenzamide(87623-47-0)
• EPA Substance Registry System: N-n-propyl-2-mercaptomethylbenzamide(87623-47-0)

Safety Data

• Hazardous Substances Data: 87623-47-0(Hazardous Substances Data)

Upstream product

• 107-10-8 propylamine 
• 1194-57-6 2-thiophthalide 
• 1218-59-3 2-<(Benzylthio)methyl>benzoic acid 

Downstream Products

• 87623-48-1 2-Mercaptomethyl-N-(2-methoxy-ethyl)-benzamide 
• 1194-57-6 2-thiophthalide 
• 107-10-8 propylamine 

Relevant articles and documents

Intramolecular participation by the thiol group in amide hydrolysis: the general acid-catalyzed pathway

The hydrolysis of N-n-propyl-2-mercaptomethylbenzamide has been investigated in HCl and a series of buffers over the pH region 0-8.5 at 40.0 deg C, μ=1.0.Nucleophilic participation by the thiol group during amide hydrolysis produces 2-thiophthalide as the stable product.The second-order rate constant for the acid-catalyzed reaction is 107 times greater than that for the hydrolysis of N-propylbenzamide.The pH-rate profile and buffer catalysis data are indicative of a change in rate-determining step near pH 3-3.5 from the uncatalyzed formation of neutral tetrahedral intermediate at low pH to its general acid-catalyzed breakdown (or a kinetic equivalent) at high pH.The Bronsted catalysis plot for this latter process is most consistent with rate-determining general base-catalyzed breakdown of the cationic tetrahedral intermediate directly to product.