13293-96-4

Basic information

• Product Name: 2-({[(E)-phenylmethylidene]amino}methyl)phenol
• CAS NO: 13293-96-4
• Molecular Formula: C₁₄H₁₃NO
• Molecular Weight: 211.2591
• Mol File: 13293-96-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 361.8°C at 760 mmHg
• Flash Point: 227.5°C
• Density: 1.04g/cm³
• Vapor Pressure: 9.68E-06mmHg at 25°C
• Refractive Index: 1.562
• CAS DataBase Reference: 2-({[(E)-phenylmethylidene]amino}methyl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-({[(E)-phenylmethylidene]amino}methyl)phenol(13293-96-4)
• EPA Substance Registry System: 2-({[(E)-phenylmethylidene]amino}methyl)phenol(13293-96-4)

Safety Data

• Hazardous Substances Data: 13293-96-4(Hazardous Substances Data)

Usage

Compound type

Phenolic compound

Structure

Benzaldehyde group and amino group connected to a benzene ring

Usage

Research and industrial applications

Potential biological activities

Antimicrobial agent

Synthesis

Organic compounds

Material development

New materials

Molecular structure

Interesting for further investigation and potential applications in various fields.

Upstream product

• 90-02-8 salicylaldehyde 
• 21013-96-7 (E)-2-hydroxylbenzaldehyde oxime 
• 932-30-9 2-Hydroxybenzylamine 
• 100-52-7 benzaldehyde 

Downstream Products

• 14680-19-4 3-benzoyl-2-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazine 

Relevant articles and documents

Hydrogen bonding in Schiff bases - NMR, structural and experimental charge density studies

A series of sixteen Schiff bases (derivatives of salicylaldehydes and aryl amines) was studied to reveal the influence of substituents and the length of the linker on the properties of the H-bonding formed. In theory, two groups of compounds, derivatives of 2-(2-hydroxybenzylidenoamine)phenol) and 2-hydroxy-N-(2-hydroxybenzylideno)benzylamine, can form different types of H-bonds using one or two hydroxyl groups present in the molecules. Two other groups of compounds, derivatives of 4-(2-hydroxybenzylidenoamine)phenol and N-(2-hydroxybenzyideno)benzylamine, can form only one type of H-bond. It was confirmed by 15N and 13C NMR experiments, that in all cases only traditional, H-bonded six-membered chelate rings were formed. The positions of the hydrogen atom in the rings depend on the substituent and phase. Generally, the OH H-bond form dominates in solution, with exception of the nitro derivatives, where the NH tautomer is present. In the solid state the tautomeric equilibrium is strongly shifted to the NH form. Only for the 5-Br derivative of one compound was the reverse relationship found. According to the results of experimental charge density investigations, two intramolecular H-bonds in the 5-methoxy derivative of 2-hydroxy-N-(2′-hydroxybenzylideno) benzylamine) differ significantly in terms of charge density properties. The intra- and intermolecular H-bonds formed by the deprotonated oxygen atom from 2-OH group are strong, with significant charge density concentration at the bond critical point and a straight, well-defined bond path, whereas the second intramolecular H-bond formed by the oxygen atom from the 2′-OH group is quite weak, with ca. five times smaller charge density concentration than in the previous case and a bent bond path. In terms of energy densities, the latter H-bond appears to be a non-bonding interaction, with total energy density being slightly positive. In terms of source contributions to the density at the H-bond critical point from the atoms involved, the intermolecular, linear H-bond is very strong and charge-assisted in the source function classification, the N(1)-H(1N)...O(1) H-bond is medium-strength, while the third H-bond is extremely weak.