86120-19-6

Basic information

• Product Name: Benzaldehyde, 4-nitro-, O-(phenylmethyl)oxime
• CAS NO: 86120-19-6
• Molecular Formula: C14H12N2O3
• Molecular Weight: 256.261
• Mol File: 86120-19-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzaldehyde, 4-nitro-, O-(phenylmethyl)oxime(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 4-nitro-, O-(phenylmethyl)oxime(86120-19-6)
• EPA Substance Registry System: Benzaldehyde, 4-nitro-, O-(phenylmethyl)oxime(86120-19-6)

Safety Data

• Hazardous Substances Data: 86120-19-6(Hazardous Substances Data)

Upstream product

• 5555-72-6 N-benzyloxycarbamic acid ethyl ester 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 555-16-8 4-nitrobenzaldehdye 
• 1129-37-9 4-nitrobenzaldehyde oxime 
• 100-44-7 benzyl chloride 
• 71-43-2 benzene 
• 1129-37-9 4-nitrobenzaldoxime 
• 60-29-7 diethyl ether 
• 141-52-6 sodium ethanolate 
• 100-39-0 benzyl bromide 
• 622-33-3 N-benzyloxyamine 
• 1129-37-9 4-nitrobenzaldehyde oxime 

Downstream Products

• 52805-36-4 4-benzyloxybenzonitrile 
• 1085338-46-0 C₁₄H₁₄N₂O 

Relevant articles and documents

Indoline Catalyzed Acylhydrazone/Oxime Condensation under Neutral Aqueous Conditions

Acylhydrazones formation has been widely applied in materials science and biolabeling. However, their sluggish condensation rate under neutral conditions limits its application. Herein, indolines with electron-donating groups are reported as a new catalyst scaffold, which can catalyze acylhydrazone, hydrazone, and oxime formation via an iminium ion intermediate. This new type of catalyst showed up to 15-fold rate enhancement over the traditional anilinecatalyzed reaction at neutral conditions. The identified indoline catalyst was successfully applied in hydrogel formation.

Synthesis and Antimicrobial Activities of Oximes Derived from O- Benzylhydroxylamine as FabH Inhibitors

Forty-three oxime derivatives were synthesized by allowing O-benzylhydroxylamines to react with primary benzaldehydes or salicylaldehydes; these products were gauged as potential inhibitors of β-ketoacyl-(acyl-carrier-protein) synthaseIII (FabH). Among the 43 compounds, 38 are reported herein for the first time. These compounds were assayed for antimicrobial activities against Escherichia coli, Pseudomonas aeruginosa, Pseudomonas fluorescens, Bacillus subtilis, Staphylococcus aureus, and Enterococcus faecalis. Compounds with prominent antibacterial activities were tested for their E. coli FabH inhibitory activities. 3-((2,4 Dichlorobenzyloxyimino) methyl) benzaldehyde O-2,4-dichlorobenzyl oxime (44) showed the best antibacterial activity, with minimum inhibitory concentrations of 3.13-6.25μgmL-1 against the tested bacterial strains, exhibiting the best E. coli FabH inhibitory activity, with an IC50 value of 1.7mM. Docking simulations were performed to position compound 44 into the E. coli FabH active site in order to determine the most probable binding conformation.

C-ACYLATION OF AZOMETHINE GROUP IN O-BENZYL AROMATIC ALDOXIMES

Reaction of four O-benzyl aromatic aldoximes with phthalimidoacetyl chloride, 3,5-dinitrobenzoyl chloride or phthalimidoacetic-p-toluenesulfonyl anhydride in the presence of triethylamine afforded moderate yields of C-acylation products of the azomethine group.Mechanism of the reaction is discussed.