782-75-2

Basic information

• Product Name: 6-{[(3-hydroxyphenyl)amino]methylidene}cyclohexa-2,4-dien-1-one
• CAS NO: 782-75-2
• Molecular Formula: C₁₃H₁₁NO₂
• Molecular Weight: 213.2319
• Mol File: 782-75-2.mol

Chemical Properties

• Boiling Point: 410.5°C at 760 mmHg
• Flash Point: 202.1°C
• Density: 1.398g/cm³
• Vapor Pressure: 2.52E-07mmHg at 25°C
• Refractive Index: 1.785
• CAS DataBase Reference: 6-{[(3-hydroxyphenyl)amino]methylidene}cyclohexa-2,4-dien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-{[(3-hydroxyphenyl)amino]methylidene}cyclohexa-2,4-dien-1-one(782-75-2)
• EPA Substance Registry System: 6-{[(3-hydroxyphenyl)amino]methylidene}cyclohexa-2,4-dien-1-one(782-75-2)

Safety Data

• Hazardous Substances Data: 782-75-2(Hazardous Substances Data)

Upstream product

• 90-02-8 salicylaldehyde 
• 64-19-7 acetic acid 
• 591-27-5 m-Hydroxyaniline 

Downstream Products

• 74646-95-0 6-phenyl-5,7-dioxa-3-aza-6-bora-1(1,2),4(1,3)-dibenzena-cycloheptaphan-2-ene 
• 1253610-23-9 [(n-butyl)8(tin)4(O)4(salicylamino(meta-(O)C₄H₄)4] 
• 947686-33-1 (2-((E)-(3-hydroxyphenylimino)methyl)phenolate)2Pd 

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The antioxidative capacity and structure-activity relationships of ten Schiff bases were investigated experimentally and theoretically. All compounds contain the aniline moiety, while the aldehyde part is either salicylaldehyde or vanillin. The DPPH assay was used to test the potential antioxidative activity of these compounds, and DFT study was used to investigate their electronic structures and provide insight into their structure-activity relationships. The effect of the position of the hydroxy, as well other groups present, on the antioxidative activity was examined. The possible radical scavenging mechanism was determined in polar (water and methanol), and nonpolar (benzene) solvents. Based on the experimental and computational results, compounds 7 and 8 exhibit the highest radical scavenging properties.

Synthesis, antioxidant and antibacterial activities of some Schiff bases containing hydroxyl and methoxy groups

A series of Schiff bases were synthesized from different aromatic amines and aromatic aldehydes containing hydroxyl and methoxy groups. These compounds were characterized by IR and 1H NMR. All the compounds were screened for in vitro antioxidant activity using DPPH method and total reducing power activity based on the ability of compounds to reduce the Fe3+-TPTZ complex to the Fe2+/ferrous. Compounds substituted with hydroxyl and other electron donating groups, such as, methoxy groups showed low to high antioxidant activity. In addition, the compounds have been screened for their antibacterial activity against strains of Escherichia coli, Methycillinresistant Staphylococcus aureus, Klebsiella pneumonia and Pseudomonas aeruginosa. The tested Schiff bases at 5 mg/disc showed different antibacterial activities depending on the type of the tested bacterial species. However, E. coli appeared to be sensitive to seven compounds (Ia, Ib, Ic, Id, If, IIb and IIe), while methicillin resistant Staphylococcus aureus (MRSA) was affected by Ic, Ie, IIc and IIe compound. On the other hand, the compounds Ia, Ic, Id, Ie and IIh revealed antibacterial activity against Klebsiella spp. The Pseudomonas aeruginosa was not sensitive to any of the tested Schiff bases.

Antioxidant activities and transition metal ion chelating studies of some hydroxyl Schiff base derivatives

Several hydroxyl Schiff base (HSB) compounds (1-10) with good radical scavenging activity (RSA) were designed. Compounds 6, 7, and 10 showed better RSAs than the common synthetic antioxidant 2,6-diterbutyl- 4-methylphenol (BHT) in DPPH and ABTS assays. To probe whether these HSB compounds may exert their antioxidant effect through transition metal ion chelation, the copper and ferrous chelating abilities of them were investigated. It was found by fluorescence quenching spectra that the binding constants Ka were in the range of 0.85×103-7.30×104 M-1. Further study was carried out by the complexation of a representative compound 5 with ferrous ion in mass spectrum. A 2:1 5-ferrous complex was readily formed in a methanol-water solution (v:v, 8:2), which confirmed that the chelation happened when the HSB compounds were treated with transition metal ions. The above results indicated that the transition metal ion chelation play an important role in their antioxidant abilities. Springer Science+Business Media, LLC 2011.