19479-87-9

Basic information

• Product Name: 1-(aminooxy)ethanone
• CAS NO: 19479-87-9
• Molecular Formula: C₂H₅NO₂
• Molecular Weight: 75.0666
• Mol File: 19479-87-9.mol

Chemical Properties

• Boiling Point: 99°C at 760 mmHg
• Flash Point: 18.3°C
• Density: 1.092g/cm³
• Vapor Pressure: 39.1mmHg at 25°C
• Refractive Index: 1.399
• CAS DataBase Reference: 1-(aminooxy)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(aminooxy)ethanone(19479-87-9)
• EPA Substance Registry System: 1-(aminooxy)ethanone(19479-87-9)

Safety Data

• Hazardous Substances Data: 19479-87-9(Hazardous Substances Data)

Upstream product

• 625-60-5 ethyl thioacetate 
• 75-36-5 acetyl chloride 
• 17336-14-0 2-carboxy-4-nitrophenyl acetate 
• 1734-62-9 2-acetoxy-5-chloro-benzoic acid 
• 17336-15-1 5-methoxyaspirin 
• 448-40-8 2-acetoxy-5-fluoro benzoic acid 
• 50-78-2 aspirin 

Downstream Products

• 21251-12-7 N-benzoyl-O-acetylhydroxylamine 
• 546-88-3 acetylhydroxamic acid 
• 6711-33-7 N-acetyl-N-hydroxyacetamide 

Relevant articles and documents

The reaction of hydroxylamine with aspirin

Hydroxylamine reacts with aspirin in aqueous solution at 25 °C predominantly through oxygen, to give O-acetylhydroxylamine as the initial product (Scheme 3). The reaction is much faster than the intramolecular general base catalysed hydrolysis of the carboxylate anion, as it is also for the CO2H form of aspirin. Both reactions are faster than expected, consistent with moderate activation and/or proton transfer catalysis of hydroxylaminolysis by both CO2- and CO2H groups. Calculations support oxygen attack as the preferred reaction, but do not permit a clear choice between mechanisms involving NH2OH and +NH3-O- as the effective nucleophile. ARKAT-USA, Inc.

Nucleophilic Reactivity toward Acetyl Chloride in Water

Rate constant ratios for the reactions of acetyl chloride with nucleophilic reagents in water containing 2.5percent (v/v) dioxane were determined by product analysis.The rate constants show a small dependence on the basicity of primary amines, with βnuc=0.25, and are assigned to rate-limiting attack of the nucleophile.Pyridines with pKa>5 behave similarly, with βnuc=0.24, but less basic pyridines react more slowly.Several "α-effect" amines and anionic oxygen nucleophiles show small rate enhancements that are attributed to increases in the rate of nucleophilic attack.The rate constants do not fit the N+ correlation equation, and it is concluded that the reactions of nucleophilic reagents with acyl compounds are not satisfactorily correlated by simple modifications of this equation.

Nuclear magnetic resonance study of addition-cyclization involving ethyl thioacetoacetate and α-nucleophiles

Addition of NH2NH2 or NH2OH to ethyl thioacetoacetate to form the corresponding cyclic product, 3-methylpyrazol-5-one or 3-methylisoxazol-5-one proceeds via cyclization of the carbinolamine formed by addition to the β-keto carbon, i.e., cyclization is faster than dehydration of the carbinolamine to form the imine.In contrast the corresponding carbinolamine derived from ethylacetoacetate undergoes dehydration faster than cyclization.By means of 1H nuclear magnetic resonance spectroscopy, it is possible to detect the cyclic carbinolamine as well as another transient and measure their rates of decay.Based on these results, a mechanism is proposed.