141891-22-7

Basic information

• Product Name: Acetic acid, [[(phenylmethylene)amino]oxy]-, (E)-
• CAS NO: 141891-22-7
• Molecular Formula: C9H9NO3
• Molecular Weight: 179.175
• Mol File: 141891-22-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Acetic acid, [[(phenylmethylene)amino]oxy]-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, [[(phenylmethylene)amino]oxy]-, (E)-(141891-22-7)
• EPA Substance Registry System: Acetic acid, [[(phenylmethylene)amino]oxy]-, (E)-(141891-22-7)

Safety Data

• Hazardous Substances Data: 141891-22-7(Hazardous Substances Data)

Upstream product

• 79-11-8 chloroacetic acid 
• 932-90-1 Benzaldoxime 
• 100-52-7 benzaldehyde 
• 7748-25-6 potassium chloroacetate 
• 645-88-5 aminooxyacetic acid 
• 141891-07-8 benzylidenaminooxy-acetic acid ethyl ester 
• 932-90-1 syn-benzaldehyde oxime 
• 79-08-3 bromoacetic acid 

Downstream Products

• 7664-41-7 ammonia 
• 100-52-7 benzaldehyde 
• 79-14-1 glycolic Acid 
• 100-47-0 benzonitrile 
• 17952-19-1 (C₄H₉)3SnOOCCH₂ONCHC₆H₅ 
• 298-12-4 Glyoxilic acid 
• 1357348-99-2 ethyl 4-[[2-[[(1-phenylmethylidene)amino]oxy]acetyl]oxy]butanoate 
• 1357348-97-0 ethyl 2-[[2-[[(1-phenylmethylidene)amino]oxy]acetyl]oxy]acetate 
• 1357348-98-1 ethyl 2-[[2-[[(1-phenylmethylidene)amino]oxy]acetyl]oxy]propionate 
• 645-88-5 aminooxyacetic acid 

Relevant articles and documents

Imino-oxy acetic acid dealkylation as evidence for an inner-sphere alcohol intermediate in the reaction catalyzed by peptidylglycine α-hydroxylating monooxygenase

Peptidylglycine α-hydroxylating monooxygenase (PHM, EC 1.14.17.3) catalyzes the stereospecific hydroxylation of a glycyl α-carbon in a reaction that requires O2 and ascorbate. Subsequent dealkylation of the α-hydroxyglycine by another enzyme, peptidylamidoglycolate lyase (PAL. EC 4.3.2.5), yields a bioactive amide and glyoxylate. PHM is a noncoupled, type II dicopper monooxygenase which activates O2 at only a single copper atom, CuM. In this study, the PHM mechanism was probed using a non-natural substrate, benzaldehyde imino-oxy acetic acid (BIAA). PHM catalyzes the O-oxidative dealkylation of BIAA to benzaldoxime and glyoxylate with no involvement of PAL. The minimal kinetic mechanism for BIAA was shown to be steady-state ordered using primary deuterium kinetic isotope effects. The D(V/K)APPARENT, BIAA decreased from 14.7 ± 1.0 as [O2] → 0 to 1.0 ± 0.2 as [O2] → ∞ suggesting the dissociation rate constant from the PHM·BIAA complex decreases as [O2] increases; thereby, reducing the steady-state concentration of [PHM]free. BIAA was further used to differentiate between potential oxidative Cu/O species using a QM/MM reaction coordinate simulation to determine which species could yield product O-dealkylation that matched our experimental data. The results of this study provided compelling evidence for the presence of a covalently linked CuII-alkoxide intermediate with a quartet spin state responsible BIAA oxidation.

(E)-(Arylmethyleneaminoxy)acetamides as analogues of neuroleptic benzamides: Synthesis and D2-dopaminergic binding affinity

Some type B (E)-(arylmethyleneaminoxy)acetamides were synthesised as analogues of type A neuroleptic and antipsychotic benzamides, in which the aromatic group is substituted by a (methyleneaminoxy)methyl moiety (C = NOCH2, MAOMM). Theoretical studies were performed in order to verify whether conformational analogies could exist between type A and type B compounds. Type B compounds were tested for their D2-dopaminergic binding affinity which represents a valid indication of their potential neuroleptic and antipsychotic properties. Biological results indicate that the MAOMM is not able to substitute the aromatic group effectively in the field of neuroleptic benzamides. The results are discussed in the light of the structural analogies and the differences between the MAOMM and the aryl.