607-24-9

Basic information

• Product Name: 2-Nitro-1-naphthol
• Synonyms: 2-NITRO-1-NAPHTHOL;2-Nitro-1-Napthol;2-Nitronaphth-1-ol;2-Nitro-2-naphthol;1-Naphthalenol, 2-nitro-;2-Nitronaphthalen-1-ol;2-Nitro-1-naphthol,98%;2-Nitro-1-naphthol 95%
• CAS NO: 607-24-9
• Molecular Formula: C₁₀H₇NO₃
• Molecular Weight: 189.17
• EINECS: 210-131-7
• Product Categories: Benzene series;Fused Ring Systems;Organic Building Blocks;Oxygen Compounds;Phenols;Building Blocks;C9 to C20+;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 607-24-9.mol
• Article Data: 38

Chemical Properties

• Melting Point: 123-125 °C(lit.)
• Boiling Point: 324.41°C (rough estimate)
• Flash Point: 149.9 °C
• Appearance: yellow-green to ochre-brown powder and/or chunks
• Density: 1.3175 (rough estimate)
• Vapor Pressure: 5.65E-05mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.13±0.50(Predicted)
• CAS DataBase Reference: 2-Nitro-1-naphthol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitro-1-naphthol(607-24-9)
• EPA Substance Registry System: 2-Nitro-1-naphthol(607-24-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25-36
• WGK Germany: 3
• Hazardous Substances Data: 607-24-9(Hazardous Substances Data)

Usage

Chemical Properties

yellow-green to ochre-brown powder and/or chunks

Uses

2-Nitro-1-naphthol was employed as substrate for use in an amperometric 3-electrode system for the determination of alkaline phosphatase, the enzyme label most commonly used in electrochemical immunoassays. It was also used in the preparation of:di-(2-nitro-1-naphthyl) hydrogen phosphate1-(2′-methyl-3′-indenyl)-2-naphthylamine and -2-naphthol (axially chiral ligands)

Purification Methods

Crystallise the naphthol (repeatedly) from EtOH. [Beilstein 6 H 615, 6 III 2938, 6 IV 4236.]

InChI:InChI=1/C10H7NO3/c12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h1-6,12H/p-1

Upstream product

• 524-42-5 1,2-naphthoquinone 
• 85-84-7 1-phenylazo-2-naphthylamine 
• 91-20-3 naphthalene 
• 581-89-5 2-nitronaphthalene 
• 90-15-3 α-naphthol 
• 7722-84-1 dihydrogen peroxide 
• 64-19-7 acetic acid 
• 131-79-3 1-[(2-methylphenyl)azo]naphthalen-2-amine 
• 3669-52-1 4-acetyl-1-naphthol 
• 7697-37-2 nitric acid 
• 634-42-4 N-1-naphthalenyl-benzamide 
• 540-80-7 tert.-butylnitrite 
• 4323-69-7 [1]naphthyl-nitro-amine 
• 103041-08-3 5,6-dinitro-1,2,3,4-tetrahydro-naphthalene 

Downstream Products

• 605-69-6 1-hydroxy-2,4-dinitronaphthalene 
• 606-41-7 2-amino-1-naphthol 
• 605-92-5 1-Hydroxy-2-amino-naphthalin-O-sulfonsaeure 
• 287976-37-8 2-nitronaphthyl-1-p-toluenesulfonate 
• 2408302-78-1 3H-3-azadibenzo[g,ij]naphtho[2,1,8-cde]azulene 
• 3574-03-6 2-phenylnaphthylene<2.1-d>oxazole 

Relevant articles and documents

The synthesis and properties of 4 acetoxy 2,3 dihydro 3 oxo 4H naphth[1,2 b] [1,4] oxazine, an analog of known carcinogenic hydroxamic acids

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Light-Controlled Tyrosine Nitration of Proteins

Tyrosine nitration of proteins is one of the most important oxidative post-translational modifications in vivo. A major obstacle for its biochemical and physiological studies is the lack of efficient and chemoselective protein tyrosine nitration reagents. Herein, we report a generalizable strategy for light-controlled protein tyrosine nitration by employing biocompatible dinitroimidazole reagents. Upon 390 nm irradiation, dinitroimidazoles efficiently convert tyrosine residues into 3-nitrotyrosine residues in peptides and proteins with fast kinetics and high chemoselectivity under neutral aqueous buffer conditions. The incorporation of 3-nitrotyrosine residues enhances the thermostability of lasso peptide natural products and endows murine tumor necrosis factor-α with strong immunogenicity to break self-tolerance. The light-controlled time resolution of this method allows the investigation of the impact of tyrosine nitration on the self-assembly behavior of α-synuclein.

Preparation method of 1-nitro-2-naphthol derivative

The invention belongs to the field of organic synthesis and in particular relates to a preparation method of a 1-nitro-2-naphthol derivative. The preparation method comprises the following steps: adding a 2-naphthol derivative shown as a formula I-1, tert-butyl nitrite and a certain amount of water into a dry reactor; adding a certain amount of an organic solvent and stirring at room temperature (commonly referring to 20 DEG C to 25 DEG C) for a period of time; after reacting, filtering an reaction solution through a glass dropper filled with silica gel; washing a filter cake with ethyl acetate; spinning and drying filtrate; carrying out silica gel column chromatography separation to obtain a target product with a formula I. A reaction formula can be shown in the description.

Preparation method of 2-nitro-1-naphthol derivative

The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of a 2-nitro-1-naphthol derivative. The preparation method comprises the following steps: adding a 1-naphthol derivative shown in Formula II-1, tert-butyl nitrite and a certain amount of water into a dry reactor, then adding a certain amount of organic solvent, and stirring at room temperature (generally 20-25 DEG C) for some time; and after the reaction is completed, filtering the reaction solution through a silica gel loaded glass dropper, flushing the filter cake with ethyl acetate, performing spin drying on the filtrate, and performing silica gel column chromatographic separation to obtain a target product shown in Formula II. The reaction formula is shown in the specification.