5290-66-4

Basic information

• Product Name: 2,4-Bis(phenylazo)naphthalene-1-ol
• Synonyms: 2,4-Bis(phenylazo)-1-naphthol;2,4-Bis(phenylazo)naphthalene-1-ol;1-Naphthalenol, 2,4-bis(2-phenyldiazenyl)-;1-Naphthalenol, 2,4-bis(phenylazo)-
• CAS NO: 5290-66-4
• Molecular Formula: C₂₂H₁₆N₄O
• Molecular Weight: 352.3886
• Mol File: 5290-66-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 507.6°Cat760mmHg
• Flash Point: 260.8°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: 2,4-Bis(phenylazo)naphthalene-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Bis(phenylazo)naphthalene-1-ol(5290-66-4)
• EPA Substance Registry System: 2,4-Bis(phenylazo)naphthalene-1-ol(5290-66-4)

Safety Data

• Hazardous Substances Data: 5290-66-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H16N4O/c27-22-19-14-8-7-13-18(19)20(25-23-16-9-3-1-4-10-16)15-21(22)26-24-17-11-5-2-6-12-17/h1-15,23H/b25-20+,26-24+

Upstream product

• 2684-02-8 benzenediazonium 
• 90-15-3 α-naphthol 
• 100-34-5 benzene diazonium chloride 
• 3375-23-3 2-phenylazo-1-naphthol 
• 130-15-4 [1,4]naphthoquinone 
• 3651-02-3 4-Phenylazo-1-naphthol 
• 86-48-6 1-hydroxy-2-naphthoic acid 
• 4870-50-2 1-hydroxy-4-phenylazo-[2]naphthoic acid 
• 305-80-6 4-diazobenzenesulfonic acid 

Downstream Products

• 6532-66-7 2.4-diamino-1-oxy-naphthalene 
• 62-53-3 aniline 

Relevant articles and documents

Physical Quenching and Chemical Reaction of Singlet Molecular Oxygen with Azo Dyes

The quenching rate constants of singlet oxygen liefetime by dialkylamino azo dyes 1 and tautomeric azo dyes 2 and 5 (as well as azo- and hydrazone-model methylated derivatives 3 and 4) were determined by measuring the 1.27-μm 1O2 emission lifetime, and the values obtained are in the range 106 - 108 M-1 s-1.The quenching involves a charge-transfer interaction, and different correlations with the oxidation potentials of the two classes of azo dyes are observed.Chemical reactions take place with a rate in the range 103 - 104 M-1 s-1 and are rationalized as a secondary pathway for the charge-transfer complex between 1O2 and the azo dye.Products include dealkylated amino azo dyes 6 from 1; compounds arising from the fragmentation of the aryl-azo bond, viz., benzenes 7 and phenoles 8 from 1 and 2; and 1,4-naphthoquinone 10 as well as the dimer 9 and the oxidized cyclic derivative 11 from 2.The methoxy derivative 3 yields an endoperoxide, which rearranges to a 1,2-naphthoquinone derivative 14.The results are discussed in comparison with the currently accepted mechanism for the reaction of 1O2 with azo dyes.