3246-76-2

Basic information

• Product Name: ethyl 4-{[(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino}benzoate
• CAS NO: 3246-76-2
• Molecular Formula: C₁₆H₁₅NO₃
• Molecular Weight: 269.2952
• Mol File: 3246-76-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 431.8°C at 760 mmHg
• Flash Point: 214.9°C
• Density: 1.291g/cm³
• Vapor Pressure: 1.17E-07mmHg at 25°C
• Refractive Index: 1.68
• CAS DataBase Reference: ethyl 4-{[(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino}benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-{[(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino}benzoate(3246-76-2)
• EPA Substance Registry System: ethyl 4-{[(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino}benzoate(3246-76-2)

Safety Data

• Hazardous Substances Data: 3246-76-2(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 90-02-8 salicylaldehyde 
• 94-09-7 p-aminoethylbenzoate 

Downstream Products

• 168646-65-9 WOCl₃(C₁₆H₁₄NO₃) 
• 111267-20-0 {Ru(C₂H₅O₂CC₆H₄NCHC₆H₄O)3} 

Relevant articles and documents

Optimizing the structure of (salicylideneamino)benzoic acids: Towards selective antifungal and anti-staphylococcal agents

An increasing resistance of human pathogenic bacteria and fungi has become a global health problem. Based on previous reports of 4-(salicylideneamino)benzoic acids, we designed, synthesised and evaluated their me-too analogues as potential antimicrobial agents. Forty imines derived from substituted salicylaldehydes and aminobenzoic acids, 4-aminobenzoic acid esters and 4-amino-N-phenylbenzamide were designed using molecular hybridization and prodrug strategies. The target compounds were synthesized with high yields and characterized by spectral methods. They were investigated against a panel of Gram-positive and Gram-negative bacteria, mycobacteria, yeasts and moulds. The most active imines were tested to determine their cytotoxicity and selectivity in HepG2 cells. Dihalogenosalicylaldehydes-based derivatives showed potent broad-spectrum antimicrobial properties, particularly against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (minimum inhibitory concentrations, MIC, from 7.81 μM) and Enterococcus faecalis (MIC of ≥15.62 μM), yeasts (MIC from 7.81 μM) and Trichophyton interdigitale mould (MIC of ≥3.90 μM). Methyl 4-[(2-hydroxy-3,5-diiodobenzylidene)amino]benzoate 4h exhibited excellent in vitro activity along with low toxicity to mammalian cells. This compound is selective for staphylococci, Candida spp. and Trichophyton interdigitale. In addition, this imine was evaluated as a potential inhibitor of Gram-positive biofilms. The successful approach used provided some promising derivatives with more advantageous properties than the parent 4-(salicylideneamino)benzoic acids.