3-Hydroxy-4-[(2-methyl-5-nitrophenyl)azo]-N-phenylnaphthalene-2-carboxamide

Base Information

• Chemical Name: 3-Hydroxy-4-[(2-methyl-5-nitrophenyl)azo]-N-phenylnaphthalene-2-carboxamide
• CAS No.: 6448-95-9
• Deprecated CAS: 67621-55-0,253683-89-5,1256701-52-6,1638971-49-9,253683-89-5
• Molecular Formula: C24H18N4O4
• Molecular Weight: 426.431
• European Community (EC) Number: 229-245-3
• UNII: 81W2C75HEQ
• DSSTox Substance ID: DTXSID1052329
• Nikkaji Number: J34.066I
• Wikidata: Q27269269
• Mol file: 6448-95-9.mol

Synonyms:Devil's Red;Pigment Red 22

Chemical Property of 3-Hydroxy-4-[(2-methyl-5-nitrophenyl)azo]-N-phenylnaphthalene-2-carboxamide

Chemical Property:

• Vapor Pressure: 4.28E-16mmHg at 25°C
• Refractive Index: 1.674
• Boiling Point: 622.6 °C at 760 mmHg
• PKA: 10.65±0.50(Predicted)
• Flash Point: 330.3 °C
• PSA: 119.87000
• Density: 1.34 g/cm³
• LogP: 7.02590
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 426.13280507
• Heavy Atom Count: 32
• Complexity: 690

Purity/Quality:

96% ^*data from raw suppliers

PigmentRed22 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)[N+](=O)[O-])N=NC2=C(C(=CC3=CC=CC=C32)C(=O)NC4=CC=CC=C4)O
• Uses: Pigment Red 22 is used in method for increasing solubility of industrial azo pigments for NMR spectra and assignments of their NMR peaks.

Technology Process of 3-Hydroxy-4-[(2-methyl-5-nitrophenyl)azo]-N-phenylnaphthalene-2-carboxamide

There total 3 articles about 3-Hydroxy-4-[(2-methyl-5-nitrophenyl)azo]-N-phenylnaphthalene-2-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 61.7%

2,3-oxynaphthoic acid phenylamide (92-77-3) + 2-methyl-5-nitrobenzenediazonium tetrafluoroborate → 4-(2-methyl-5-nitrophenyl)azo-3-hydroxy-N-phenylnaphthalene-2-carboxamide (6448-95-9)

Guidance literature:

2,3-oxynaphthoic acid phenylamide; With sodium hydroxide; In 1-methyl-pyrrolidin-2-one; at 40 ℃;

2-methyl-5-nitrobenzenediazonium tetrafluoroborate; In 1-methyl-pyrrolidin-2-one; at 5 - 20 ℃;

DOI:10.1016/j.molstruc.2014.12.011

Reference yield:

2,3-oxynaphthoic acid phenylamide (92-77-3) → 4-(2-methyl-5-nitrophenyl)azo-3-hydroxy-N-phenylnaphthalene-2-carboxamide (6448-95-9)

Guidance literature:

Reference yield:

→ 4-(2-methyl-5-nitrophenyl)azo-3-hydroxy-N-phenylnaphthalene-2-carboxamide (6448-95-9)

Guidance literature:

2-Methyl-5-nitro-anilin, Naphthol AS, 1.) NaNO2, HCl, NaOH in W., 2.) Erhitzen bei 100grad;

upstream raw materials:

2,3-oxynaphthoic acid phenylamide

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