124617-83-0

Basic information

• Product Name: N-ACETOXY-N-ETHOXYBENZAMIDE
• Synonyms: N-ACETOXY-N-ETHOXYBENZAMIDE
• CAS NO: 124617-83-0
• Molecular Formula: C₁₁H₁₃NO₄
• Molecular Weight: 223.23
• Mol File: 124617-83-0.mol

Chemical Properties

• Boiling Point: 290.7°Cat760mmHg
• Flash Point: 129.6°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 0.00204mmHg at 25°C
• Refractive Index: 1.524
• CAS DataBase Reference: N-ACETOXY-N-ETHOXYBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETOXY-N-ETHOXYBENZAMIDE(124617-83-0)
• EPA Substance Registry System: N-ACETOXY-N-ETHOXYBENZAMIDE(124617-83-0)

Safety Data

• Hazardous Substances Data: 124617-83-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 2649, 1989 DOI: 10.1016/S0040-4039(00)99089-0

InChI:InChI=1/C11H13NO4/c1-3-15-12(16-9(2)13)11(14)10-7-5-4-6-8-10/h4-8H,3H2,1-2H3

Upstream product

• 563-63-3 silver(I) acetate 
• 124617-87-4 ethyl N-chlorobenzohydroxamate 
• 127-09-3 sodium acetate 
• 93-89-0 benzoic acid ethyl ester 
• 32685-16-8 potassium benzohydroxamate 
• 22509-51-9 O-ethyl benzoylhydroxamic acid 

Downstream Products

• 64-19-7 acetic acid 
• 93-89-0 benzoic acid ethyl ester 
• 5579-27-1 1,4-dimethyl-1,4-diphenyl-2-tetrazine 

Relevant articles and documents

N-ACETOXY-N-ALKOXYAMIDES - A NEW CLASS OF NITRENIUM ION PRECURSORS WICH ARE MUTAGENIC

N-chloro-O-alkylbenzohydroxamates react with silver acetate in ether giving N-acetoxy-N-alkoxybenzamides which, by analogy with N,O-diacyl-N-arylhydroxylamines, have been shown to be mutagenic in the Ames test.

Acyloxy group exchange in N-acyloxy-N-alkoxyamides

Acyloxy group exchange at the nitrogen atom proceeds in the interaction of N-acyloxy-N-alkoxyureas, N-acyloxy-N-alkoxybenzamides and N-acyloxy-N- alkoxycarbamates with Na and K carboxylates in MeCN.

Geminal systems 50. Synthesis and alcoholysis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and benzamides

Procedures were developed for the synthesis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and benzamides by the reactions of the corresponding N-alkoxy-N-chloro derivatives with sodium carboxylates in MeCN. N-Chloro-N-ethoxy-p-toluenesulfonamide was inert in this reaction. Alcoholysis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and tert-alkylamines afforded the corresponding N,N-dialkoxy derivatives, whereas alcoholysis of N-acetoxy-N-ethoxybenzamide gave rise to alkyl benzoates.

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.