151726-58-8

Basic information

• Product Name: 2-HYDROXY-5-PHENYLAZOBENZALDEHYDE
• Synonyms: CBI-BB ZERO/001077;2-HYDROXY-5-PHENYLAZOBENZALDEHYDE;2-HYDROXY-5-[(1E)-PHENYLDIAZENYL]BENZALDEHYDE;TIMTEC-BB SBB001599;5-[(1E)-Phenyldiazenyl]salicylaldehyde;2-Hydroxy-5-[(E)-phenyldiazenyl]benzaldehyde
• CAS NO: 151726-58-8
• Molecular Formula: C₁₃H₁₀N₂O₂
• Molecular Weight: 226.23
• Mol File: 151726-58-8.mol
• Article Data: 26

Chemical Properties

• Melting Point: 128-130 °C
• Boiling Point: 398.021°C at 760 mmHg
• Flash Point: 194.517°C
• Appearance: /
• Density: 1.198g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.606
• PKA: 7.19±0.18(Predicted)
• CAS DataBase Reference: 2-HYDROXY-5-PHENYLAZOBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-5-PHENYLAZOBENZALDEHYDE(151726-58-8)
• EPA Substance Registry System: 2-HYDROXY-5-PHENYLAZOBENZALDEHYDE(151726-58-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 151726-58-8(Hazardous Substances Data)

Usage

General Description

2-HYDROXY-5-PHENYLAZOBENZALDEHYDE, also known as Sudan I, is an organic compound commonly used as a dye and colorant in various industries. It is a yellowish-orange powder with a characteristic azo structure and an aldehyde functional group. Sudan I has been found to have potential carcinogenic and mutagenic properties, leading to its restriction and even banning in food and cosmetic products in some countries. Its main application is in the coloring of solvents, plastics, waxes, oils, and gasoline, but it is also used as a stain for lipids and fats in histology. Sudan I has also been used as a marker for the detection of red blood cells and platelets in biological samples. Due to its potential health risks, there is ongoing research and regulation to limit exposure to Sudan I in various consumer products.

InChI:InChI=1/C13H10N2O2/c16-9-10-8-12(6-7-13(10)17)15-14-11-4-2-1-3-5-11/h1-9,17H/b15-14+

Upstream product

• 100-34-5 benzene diazonium chloride 
• 90-02-8 salicylaldehyde 
• 62-53-3 aniline 
• 1351524-00-9 C₁₃H₁₀N₂O₂ 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 

Downstream Products

• 38501-90-5 2-[(E)-(hydroxyimino)methyl]-4-[(E)-phenyldiazenyl]phenol 

Relevant articles and documents

An azo-azomethine ligand and its copper(II) complex: Synthesis, X-ray crystal structure, spectral, thermal, electrochemical and photoluminescence properties

Abstract In this study, a new azo-azomethine ligand, 4-[(E)-phenyldiazenyl]-2-[(E)-{[4-(propan-2-yl)phenyl]imino}methyl]phenol (HL) and its Cu(II) complex, [CuL2] were synthesized and characterized by the analytical and spectroscopic methods su

Synthesis, characterization and antimicrobial studies of 2-{(E)-[(2-hydroxy-5-methylphenyl)imino]methyl}-4-[(E)-phenyldiazenyl]phenol as a novel azo-azomethine dye

A novel dye, 2-{(E)-[(2-hydroxy-5-methylphenyl)imino]methyl}-4-[(E)- phenyldiazenyl]phenol dye was synthesized by the condensation reaction of 2-hydroxy-5-[(E)-phenyldiazenyl]benzaldehyde with 2-amino-4-methylphenol in methanol. The title dye was characte

Syntheses, crystal structures, DNA binding, DNA cleavage, molecular docking and DFT study of Cu(II) complexes involving N2O4 donor azo Schiff base ligands

Here, we have reported three novel copper(ii) complexes (1-3) involving azo Schiff base ligands. All the complexes have been well characterized using different spectroscopic tools and single crystal X-ray diffraction analysis. Structural and electronic parameters of the complexes have been justified by DFT and TDDFT computation. All the complexes showed minor groove binding to the AT-rich sequence of DNA. The binding properties of the complexes have been extensively studied, and are further supported by a molecular docking analysis. These complexes also showed H2O2-mediated DNA cleavage properties involving a hydroxyl radical. MTT assay of the complexes was performed and they were found to be cytotoxic. The intrinsic binding constants (Kb) were calculated to be 7.11 × 105 M-1, 8.36 × 105 M-1 and 10.81 × 105 M-1 for complexes 1-3, respectively. The complexes show interesting supramolecular architectures in the solid state mainly supported by π-π stacking interactions.

Synthesis of two new azo-azomethines; Spectral characterization, crystal structures, computational and fluorescence studies

This study describes the preparation, characterization and the photoluminescence properties of novel azo-azomethines (2-{(E)-[(4-ethylphenyl)imino]methyl}-4-[(E)-phenyldiazenyl]phenol, HL1 and 2-{(E)-[(3-ethylphenyl)imino]methyl}-4-[(E)-phenyld

A new ESIPT-based fluorescent probe for highly selective and sensitive detection of HClO in aqueous solution

A new ESIPT-based fluorescent probe, PHC2, for the detection of hypochlorous acid has been rationally designed and developed. Endowed by the specific reaction between hypochlorous acid and phenyl azo group, PHC2 features high degree of selectivity and sensitivity for HClO with a low detection limit (13.2?nM) under physiological conditions in neutral aqueous solution.

Synthesis, spectroscopic investigation and theoretical studies of 2-((E)-(2-(2-cyanoacetyl)hydrazono)methyl)-4-((E)-phenyldiazenyl)phenyl methyl carbonate

Synthesis and computational optimization studies have been carried out by Hartree–Fock (HF) and Density Functional Theory (DFT–B3LYP) methods with 6–31+G(d, p) basis set for 2-((E)-(2-(2-cyanoacetyl)hydrazono)methyl)-4-((E)-phenyldiazenyl)phenyl methyl ca

Synthesis of new bis-benzylidene-hydrazides as a sensitive chromogenic sensor for naked-eye detection of CNˉ and AcOˉ ions

Some new bis-benzylidene-hydrazides were synthesized via a condensation reaction of the corresponding azo dyes with adipic acid dihydrazide. All compounds because of the three possible stereoisomers showed four sets of signals in NMR. The anion recognition studies exhibited that the nitro bis-benzylidene-hydrazide derivative acts as a highly sensitive and selective chromogenic sensor for naked-eye detection of CNˉ and AcOˉ ions, with a distinct color change from yellow to blue and yellow to purple, respectively. The limit of detection (LOD) was found for 1d toward CNˉ to be 1.1 μM. The result of the Job's plot indicated stoichiometry of binding between chemosensor and anions is found to be 1:2.

Charge transfer complexation between some transition metal ions with azo Schiff base donor as a smart precursor for synthesis of nano oxides: An adsorption efficiency for treatment of Congo red dye in wastewater

This mentioned article aimed to synthesized of nanostructured CuO, Co3O4 and NiO oxides based on the thermal decomposition of precursors associated from the complexation between azo Schiff base chelate (2,2′-((1E,1′E)-hydrazine-1,2-d