5348-24-3

Basic information

• Product Name: 2-{[(E)-(2-nitrophenyl)methylidene]amino}phenol
• Synonyms: 2-[(2-Nitrobenzylidene)amino]phenol
• CAS NO: 5348-24-3
• Molecular Formula: C₁₃H₁₀N₂O₃
• Molecular Weight: 242.2301
• Mol File: 5348-24-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 456.9°C at 760 mmHg
• Flash Point: 230.1°C
• Density: 1.25g/cm³
• Vapor Pressure: 5.74E-09mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: 2-{[(E)-(2-nitrophenyl)methylidene]amino}phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-{[(E)-(2-nitrophenyl)methylidene]amino}phenol(5348-24-3)
• EPA Substance Registry System: 2-{[(E)-(2-nitrophenyl)methylidene]amino}phenol(5348-24-3)

Safety Data

• Hazardous Substances Data: 5348-24-3(Hazardous Substances Data)

Usage

Yellow solid

The physical state and color of the compound, which can be useful for identification and handling.

Molecular weight

238.23 g/mol The mass of one mole of the compound, which can be used to calculate the mass of a given amount of the substance.

Used in pharmaceutical industry

The compound is utilized as an intermediate in the synthesis of various pharmaceutical products, which can provide insight into its potential applications and uses.

Used in research and development

The compound is also used as a building block for the creation of new organic compounds, which can be useful for the development of new drugs and materials.

Stable under normal conditions

The compound is stable and does not easily react or degrade under typical conditions, which can be important for handling and storage.

Handled and stored according to standard laboratory procedures

The compound should be handled and stored according to standard laboratory procedures for chemical compounds of its type, which can help ensure safety and stability.

Upstream product

• 95-55-6 2-amino-phenol 
• 552-89-6 2-nitro-benzaldehyde 

Downstream Products

• 840-37-9 2-(2′-nitrophenyl)-1,3-benzoxazole 
• 1092936-36-1 2-[2-(t-Boc-L-alanylamino)phenyl]benzoxazole 
• 1310352-09-0 2-[2-(t-Boc-β-alanylamino)phenyl]benzoxazole 
• 1085705-88-9 2-[(2-L-alanylamino)phenyl]benzoxazole 
• 29483-74-7 2-(2-aminophenyl)benzoxazole 
• 1393931-13-9 diethyl 3-(2-nitrophenyl)-3,4-dihydrobenzo[b][1,4]oxazine-2,2-dicarboxylate 
• 3094-85-7 2-hydroxy-N-(2-nitrobenzylidene)-aniline 

Relevant articles and documents

Inhibition of copper-mediated aggregation of human γD-crystallin by Schiff bases

Abstract: Protein aggregation, due to the imbalance in the concentration of Cu2+ and Zn2+ ions is found to be allied with various physiological disorders. Copper is known to promote the oxidative damage of β/γ-crystallins in aged eye lens and causes their aggregation leading to cataract. Therefore, synthesis of a small-molecule ‘chelator’ for Cu2+ with complementary antioxidant effect will find potential applications against aggregation of β/γ-crystallins. In this paper, we have reported the synthesis of different Schiff bases and studied their Cu2+ complexation ability (using UV–Vis, FT-IR and ESI-MS) and antioxidant activity. Further based on their copper complexation efficiency, Schiff bases were used to inhibit Cu2+-mediated aggregation of recombinant human γD-crystallin (HGD) and β/γ-crystallins (isolated from cataractous human eye lens). Among these synthesized molecules, compound 8 at a concentration of 100 μM had shown ~95% inhibition of copper (100?μM)-induced aggregation. Compound 8 also showed a positive cooperative effect at a concentration of 5–15 μM on the inhibitory activity of human αA-crystallin (HAA) during Cu2+-induced aggregation of HGD. It eventually inhibited the aggregation process by additional ~20%. However, ~50% inhibition of copper-mediated aggregation of β/γ-crystallins (isolated from cataractous human eye lens) was recorded by compound 8 (100 μM). Although the reductive aminated products of the imines showed better antioxidant activity due to their lower copper complexing ability, they were found to be non-effective against Cu2+-mediated aggregation of HGD. Graphical Abstract: [Figure not available: see fulltext.]

Catalyst-free allylation of 2-aminophenol–derived aldimines with allyltrichlorosilane under thermal conditions

Allylation of 2-aminophenol-derived aldimines using allyltrichlorosilane under catalyst free conditions has been developed. This reaction afforded the corresponding homoallylic amines in good to excellent yields (68–94%). The salicylaldehyde-derived aldimines as well as benzoylhydrazone also found to react with allyltrichlorosilane smoothly under the same conditions, to furnish the corresponding homoallylic amine derivatives. This study suggests that the phenolic –OH group acts as an anchoring group for the transfer of allyl group from allyl silane reagent.

Synthesis and biological activities of 2-aminophenol-based Schiff bases and their structure-activity relationship

Six Schiff bases 8-13 were synthesized by condensation of 2-aminophenol (1) with various chloro- and nitro-benzaldehydes (2-7), characterized, and evaluated for antioxidant, antibacterial, lipoxygenase, and urease inhibitory potentials. All Schiff bases e