31767-13-2

Basic information

• Product Name: methyl (2E)-(hydroxyimino)ethanoate
• CAS NO: 31767-13-2
• Molecular Formula: C₃H₅NO₃
• Molecular Weight: 103.0767
• Mol File: 31767-13-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 187.758°C at 760 mmHg
• Flash Point: 67.354°C
• Density: 1.209g/cm³
• Vapor Pressure: 0.172mmHg at 25°C
• Refractive Index: 1.437
• CAS DataBase Reference: methyl (2E)-(hydroxyimino)ethanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2E)-(hydroxyimino)ethanoate(31767-13-2)
• EPA Substance Registry System: methyl (2E)-(hydroxyimino)ethanoate(31767-13-2)

Safety Data

• Hazardous Substances Data: 31767-13-2(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 3545-80-0 hydroxyiminoacetic acid 
• 922-68-9 Methyl glyoxylate 
• 109745-70-2 methyl glyoxylate methyl hemi-acetal 
• 463-51-4 Ketene 
• 81539-54-0 isonitroso Meldrum’s acid 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 178240-01-2 methyl (E)-2-hydroxyimino-2-o-tolylacetate 
• 107046-74-2 Cyclohexyl-[(E)-hydroxyimino]-acetic acid methyl ester 

Relevant articles and documents

Acid-catalyzed aza-Diels-Alder versus 1,3-dipolar cycloadditions of methyl glyoxylate oxime with cyclopentadiene

The acid-catalyzed 1,4- and 1,3-cycloadditions between methyl glyoxylate oxime (1) and cyclopentadiene were investigated using various Lewis and/or Bronsted acids at different temperatures in dichloromethane as solvent. Besides the expected new adducts, (±)-methyl [(3-exo)-2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylate (2) and (±)-methyl [(3-endo)-2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylate (3), a third adduct, (±)-methyl (1R,4R,5R)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate (4), whose formation can be explained by a 1,3-dipolar cycloaddition, was obtained. Yields and product ratios were found to be more dependent on the catalyst than on the temperature; these results and the stereochemistry of the adducts, confirmed by spectroscopic data (1H and 13C NMR) and by X-ray crystallography, were used to analyze and propose a mechanistic explanation for both cycloadditions.

Process for the preparation of phenyl glyoxylic acid ester oximes

The invention relates to a process for the preparation of compounds of formula (I) wherein: R1is optionally substituted alkyl, R2is C1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C2alkyl, aryl, aryl-C1-C2alkyl, heterocyclyl, heterocycly-C1-C2alkyl, which groups are optionally substituted by alkyl, alkoxy, or halogen; in which process (I) an aniline of formula (II), is diazotized with an organic or inorganic nitrite or nitrous acid; (2) the resulting diazonium salt is reacted with an oxime of formula (III) in presence of a copper(II)-salt.

Synthesis of nucleosides and related compounds. XXXIV. Synthesis of 5- Isonitroso-1,3-dioxane-4,6-diones and their reactions

Synthesis of 5-isonitroso-1,3-dioxane-4,6-dione (2: isonitroso Meldrum's acid) and related compounds and their reactions were described. Compound (2) reacted with various alcohols to give hydroxyiminoacetic acid esters in moderate yields. Compound 2 was a