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

• 67-56-1 methanol 
• 607-22-7 1-chloro-2-nitronaphthalene 
• 124-41-4 sodium methylate 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 90-15-3 α-naphthol 
• 830-81-9 1-naphthyl acetate 
• 24934-47-2 1,2-dinitronaphthalene 
• 607-23-8 2-nitro-1-naphthylamine 
• 2437-30-1 N-(2-nitronaphthalen-1-yl)acetamide 
• 575-36-0 1-acetamidonaphthalene 
• 6373-60-0 1,2-naphthoquinone-2-oxime 
• 38396-17-7 N-(2-nitro-[1]naphthyl)-benzamide 
• 39139-77-0 dimethyl-(2-nitro-[1]naphthyl)-amine 

Downstream Products

• 16155-58-1 2-p-tolyl-naphtho[2,1-d]oxazole 
• 287976-37-8 2-nitronaphthyl-1-p-toluenesulfonate 
• 20686-65-1 2-methyloxazolo<4,5-a>naphthalene 
• 532932-91-5 cis-(1-carbonyl-2-oxo-1,2-diphenylethenediyl)(2-nitro-1-naphtholato)bis(trimethylphosphine)cobalt(III) 
• 532932-91-5 trans-(1-carbonyl-2-oxo-1,2-diphenylethenediyl)(2-nitro-1-naphtholato)bis(trimethylphosphine)cobalt(III) 
• 605-92-5 1-Hydroxy-2-amino-naphthalin-O-sulfonsaeure 
• 606-41-7 2-amino-1-naphthol 
• 605-69-6 1-hydroxy-2,4-dinitronaphthalene 

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.

Potassium Periodate/NaNO2/KHSO4-Mediated Nitration of Aromatic Compounds and Kinetic Study of Nitration of Phenols in Aqueous Acetonitrile

Synthesis and kinetics of potassium periodate(KIO4)/NaNO2/KHSO4)-initiated nitration of aromatic compounds have been studied in aqueous acetonitrile medium. Synthesis of nitroaromatic compounds is achieved under conventional and solvent-free microwave conditions. Reaction times in microwave-assisted reaction are comparatively less than in conventional reaction. The reaction kinetics for the nitration of phenols in aqueous bisulfate and acetonitrile medium indicated first-order dependence on [phenol], [NaNO2], and [KIO4]. An increase in [KHSO4] accelerated the rate of nitration under otherwise similar conditions. The rate of nitration increased in the solvent of high dielectric media (solvents with high dielectric constant (D)). Observed results were in accordance with Amis and Kirkwood plots [log k′ vs. (1/D) and [(D ? 1)/(2D + 1)]. These observations probably indicate the participation of anionic species and molecular or (dipolar) species in the rate-determining step. In addition, the plots of (log k′) versus volume% of organic solvent were also linear, which probably indicate the importance of both electrostatic and nonelectrostatic forces, solvent–solute interactions during nitration of phenols. Reaction rates accelerated with the introduction of electron-donating groups and retarded with electron-withdrawing groups, but results could not be quantitatively correlated with Hammett's equation and depicted deviations from linearity. These deviations could probably be attributed to cumulative effects arising inductive, resonance, and steric effects. Leffler's plot (ΔH# vs. ΔS#) was found linear indicating the compensation (cumulative) effect of both enthalpy and entropy parameters in controlling the mechanism of nitration.

Prussian Blue/NaNO2 as an Efficient Reagent for the Nitration of Phenols in Aqueous Bisulfate and Acetonitrile Medium: Synthetic and Kinetic Study

The reaction kinetics of Prussian blue (PB)/NaNO2 initiated for the nitration of phenols by in aqueous bisulfate and acetonitrile medium indicated first-order dependence on [phenol], [NaNO2], and [PB]. An increase in [KHSO4] accelerated the rate of nitration under otherwise similar conditions. The rate of nitration was faster in the solvent of higher dielectric constant (D). Observed results were in accordance with Amis and Kirkwood plots [log k′ vs. (1/D) and [(D ? 1)/(2D + 1)]. These findings together with the linearity of plots, log k′ versus (vol% of acetonitrile (ACN)) and mole fraction of (nx) ACN, probably indicate the importance of both eloctrostatic and nonelctrostatic forces, solvent–solute interactions during nitration of phenols. Reaction rates accelerated with the introduction of electron-donating groups and retarded with electron-withdrawing groups, which are interpreted by Hammett's theory of linear free energy relationship. Hammett's reaction constant (ρ) is a fairly large negative (ρ 0) value, indicating attack of an electrophile on the aromatic ring. Furthermore, an increase in temperature decreased the reaction constant (ρ) values. This trend was useful in obtaining isokinetic temperature (β) from Exner's plot of ρ versus 1/T. Observed β value (337.8 K) is above the experimental temperature range (303–323 K), indicating that the enthalpy factors are probably more important in controlling the reaction.