57139-22-7

Basic information

• Product Name: N-hydroxy-4-methoxybenzamide
• Synonyms: benzamide, N-hydroxy-4-methoxy-
• CAS NO: 57139-22-7
• Molecular Formula: C₈H₈NO₃*K
• Molecular Weight: 167.162
• Mol File: 57139-22-7.mol
• Article Data: 3

Chemical Properties

• Density: 1.24g/cm³
• Refractive Index: 1.558
• CAS DataBase Reference: N-hydroxy-4-methoxybenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxy-4-methoxybenzamide(57139-22-7)
• EPA Substance Registry System: N-hydroxy-4-methoxybenzamide(57139-22-7)

Safety Data

• Hazardous Substances Data: 57139-22-7(Hazardous Substances Data)

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 100-09-4 4-methoxybenzoic acid 
• 94-30-4 ethyl 4-methoxybenzoate 

Downstream Products

• 106274-43-5 butyl p-methoxybenzohydroxamate 
• 99986-22-8 N-<4-Methoxy-benzoyl>-O-propyl-hydroxylamin 
• 57977-21-6 N-<4-Methoxy-benzoyl>-O-propargyl-hydroxylamin 
• 59101-34-7 N,O-bis-(4-methoxy-benzoyl)-hydroxylamine 
• 1312588-28-5 N-(3,5-dimethylbenzyl)-N-methoxy-4-methoxybenzamide 
• 121-98-2 methyl 4-methoxybenzoate 
• 24056-08-4 N-methoxy-4-methoxylbenzamide 
• 10507-69-4 4-methoxybenzohydroxamic acid 
• 254455-44-2 Sn(C₆H₅)2(ClC₆H₄O)2 
• 1103-05-5 bis(benzenethiolato-κ-S)diphenyltin(IV) 
• 1441-22-1 Ph₃SnSPh 
• 131229-60-2 N-(acetyloxy)-N-butoxy-4-methoxybenzamide 
• 139259-80-6 butyl N-chloro-p-methoxybenzohydroxamate 
• 109482-59-9 C₂₁H₁₆ClNO₆S 

Relevant articles and documents

Synthesis, characterization and assessment of local anesthetic activity of some benzohydroxamic acids

In the present investigation, 6 compounds (E1-E6) were synthesized by reaction of ethyl esters of p-substituted benzoic acid with hydroxylamine. The chemical structures of the synthesized hydroxamic acids were verified on the basis of spectral analysis (IR, 1H NMR, 13C NMR and mass spectra). The benzohydroxamic acids were examined for potential local anesthetic activity using foot withdrawal reflex of the frog and benzocaine was used as standard drug. Compounds were tested at two different solvents; 5 % DMSO and 0.65 % NaOH, each solution was tested at three different concentration levels (40, 100 and 200 μg/mL). Local anesthetic activity of the compounds differed according to the concentration level and selected solvent. Compounds E4 and E5 were found to be the most active and were comparable to the standard drug in tested solvents at all investigated concentrations. All compounds displayed an enhanced activity in the the aqueous basic solutions.

Evidence for the Formation of Nitrenium Ions in the Acid-catalysed Solvolysis of Mutagenic N-Acetoxy-N-Alkoxybenzamides

In aqueous acetonitrile, N-acetoxy-N-alkoxybenzamides undergo acid-catalysed solvolysis by the AAl1 mechanism to give acetic acid and nitrenium ions.This is indicated by an inverse dependence of the acid-independent rate constant, kH, upon the activity of water, a solvent kinetic isotope effect of 0.44 and positive Σ(excit.) values.In addition, relief of steric compression at the nitrogen enhances the rate of solvolysis.Hammett correlations with ?+ substituent constants were found for the rates of solvolysis of para-substituted-N-acetoxy-N-butoxybenzamides and N-acetoxy-N-(para-substituted benzyloxy) benzamides.This fact and the low ρ-values of -1.35 and -1.56, respectively, are indicative of a strong build-up of positive charge in the transition state which has both nitrenium ion and oxonium ion character and is in accordance with computed molecular-orbital properties of N-alkoxynitrenium ions.Greater levels of mutagenicity have been measured for those compounds which are more readily solvolysed to nitrenium ions.