29644-87-9

Basic information

• Product Name: 2-{[(E)-(4-methoxyphenyl)methylidene]amino}-5-nitrophenol
• CAS NO: 29644-87-9
• Molecular Formula: C₁₄H₁₂N₂O₄
• Molecular Weight: 272.2561
• Mol File: 29644-87-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 496°C at 760 mmHg
• Flash Point: 253.8°C
• Density: 1.27g/cm³
• Vapor Pressure: 1.83E-10mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: 2-{[(E)-(4-methoxyphenyl)methylidene]amino}-5-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-{[(E)-(4-methoxyphenyl)methylidene]amino}-5-nitrophenol(29644-87-9)
• EPA Substance Registry System: 2-{[(E)-(4-methoxyphenyl)methylidene]amino}-5-nitrophenol(29644-87-9)

Safety Data

• Hazardous Substances Data: 29644-87-9(Hazardous Substances Data)

Usage

Structure

A phenol ring with a nitro group at the 5-position, an imine group (attached to the nitrogen of the amino), and a methoxy group at the 4-position of the phenol ring.

Appearance

Bright yellow color

Uses

pH indicator in analytical chemistry, potential pharmaceutical properties (antioxidant and antimicrobial activities), development of dyes, pigments, and other organic synthesis processes.

Safety

Proper handling and storage procedures should be followed to ensure safety and regulatory compliance.

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 121-88-0 5-Nitro-2-aminophenol 

Downstream Products

• 16383-89-4 5-nitro-2-amino-phenetole 
• 3315-22-8 2-(4-methoxy-phenyl)-6-nitro-benzooxazole 
• 13027-44-6 N,N'-(ethoxy-p-phenylene)-bis-benzamide 

Relevant articles and documents

Structure-activity relationships of benzimidazoles and related heterocycles as topoisomerase I poisons

A series of substituted 2-(4-methoxyphenyl)-1H-benzimidazoles were synthesized and evaluated as inhibitors of topoisomerase I. The presence of a 5-formyl-, 5-(aminocarbonyl)-, or 5-nitro group (i.e., substituents capable of acting as hydrogen bond accepters) correlated with the potential of select derivatives to inhibit topoisomerase I. In contrast to bi- and terbenzimidazoles, the substituted benzimidazoles that were active as topoisomerase I poisons exhibited minimum or no DNA binding affinity. 5-Nitro-2-(4-methoxyphenyl)-1H-benzimidazole exhibited the highest activity and was significantly more active than the 4-nitro positional isomer. The 5- and 6-nitro derivatives of 2-(4-methoxyphenyl)benzoxazole, 2-(4-methoxyphenyl)benzothiazole, and 2-(4-methoxyphenyl)indole were synthesized and their relative activity as topoisomerase I inhibitors determined. None of these heterocyclic analogues were effective in significantly inhibiting cleavable-complex formation in the presence of DNA and topoisomerase I, suggesting a high degree of structural specificity associated with the interaction of these substituted benzimidazoles with the enzyme or the enzyme-DNA complex. In evaluating their cytotoxicity, these new topoisomerase I poisons also exhibited no significant cross-resistance against cell lines that express camptothecin-resistant topoisomerase I.