6471-46-1

Basic information

• Product Name: 1-[(3-nitrophenyl)azo]-2-naphthol
• Synonyms: 1-[(3-nitrophenyl)azo]-2-naphthol;C.I.12065;Meta Nitro Orange MN;1-((m-Nitrophenyl)azo)-2-naphthol;2-Naphthalenol, 1-((3-nitrophenyl)azo)-;2-Naphthalenol, 1-(2-(3-nitrophenyl)diazenyl)-;2-Naphthol, 1-((m-nitrophenyl)azo)- (8ci);Einecs 229-312-7
• CAS NO: 6471-46-1
• Molecular Formula: C₁₆H₁₁N₃O₃
• Molecular Weight: 293.27684
• EINECS: 229-312-7
• Mol File: 6471-46-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 470.4°C at 760 mmHg
• Flash Point: 238.3°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 5.1E-09mmHg at 25°C
• Refractive Index: 1.673
• CAS DataBase Reference: 1-[(3-nitrophenyl)azo]-2-naphthol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(3-nitrophenyl)azo]-2-naphthol(6471-46-1)
• EPA Substance Registry System: 1-[(3-nitrophenyl)azo]-2-naphthol(6471-46-1)

Safety Data

• Hazardous Substances Data: 6471-46-1(Hazardous Substances Data)

Usage

General Description

1-[(3-nitrophenyl)azo]-2-naphthol is a chemical compound with the molecular formula C16H11N3O3. It is commonly known as Sudan I, an azo dye used in the production of various products such as plastics, textiles, and inks. Its chemical structure consists of a naphthol group and a nitrophenyl group linked by an azo linkage. Sudan I is known to be a potential carcinogen and has been banned in many countries due to its harmful effects on human health. Exposure to Sudan I has been linked to an increased risk of cancer, liver damage, and other adverse health effects. Therefore, its use and presence in food, cosmetics, and other products is strictly regulated.

InChI:InChI=1/C16H11N3O3/c20-15-9-8-11-4-1-2-7-14(11)16(15)18-17-12-5-3-6-13(10-12)19(21)22/h1-10,17H

Upstream product

• 16278-29-8 3-nitrobenzenediazonium 
• 573-97-7 1-bromo-2-naphthol 
• 10147-94-1 1-(3'-nitrobenzeneazo)-2-amino-naphthalene 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 135-19-3 β-naphthol 
• 99-09-2 3-nitro-aniline 
• 118488-93-0 m-nitrobenzenediazo methyl ether 
• 99779-37-0 2-((3-nitrophenylamino)methyl)phenol 

Downstream Products

• 39781-23-2 2-acetoxy-1-(3-nitro-phenylazo)-naphthalene 
• 32624-48-9 1-(3-aminophenylazo)naphthalen-2-ol 
• 84317-56-6 (2-Chloro-naphthalen-1-yl)-(3-nitro-phenyl)-diazene 

Relevant articles and documents

One-pot synthesis of azo compounds in the absence of acidic or alkaline additives

A one-pot method for the synthesis of azo compounds by the reaction of β-naphthol with aryl amines using t-BuONO as the nitrosonium source in DCM at room temperature was developed. This method features mild reaction conditions, a simple experimental procedure, and is free of acidic or alkaline additives.

Substituent effect on the tautomerization of 1-arylazonaphthalen-2-ols by mass spectrometric analysis

An electron-ionization (EI) mass spectra of a series of 1-arylazonaphthalen-2-ols was obtained for studying the substituent effect on the fragmentation. The correlation between the ratio, molecular ion and fragment ion, and Hammett's constants is applied to examine the effect of the substituent on the fragmentation. The negative correction between the ratio, Imolecular ion/(I171amu + I143amu + I115amu), and Hammett's constants indicates an electron-withdrawing group destabilized the molecular ion. An unusual long-range hydrogen transfer demonstrates an important role in the fragmentation process Mass spectra of a series of 1-arylazonaphthalen-2-ols were obtained for studying the substituent effect on the fragmentation. The correlation between the ratio of molecular ion and fragment ion, and Hammett's constants is applied to examine the effect of substituent on the fragmentation. The negative correction indicates an electron-with-drawing group destabilized the molecular ion. An unusual long-range hydrogen transfer demonstrates an important role in the fragmentation process.

Synthesis of dyes from aromatic C-nitroso-N-hydroxytriazenes

Aromatic C-nitroso-N-hydroxytriazenes can be used as stable forms of diazo compounds for preparation of azo dyes.