607-24-9

Usage

Uses

Used in Electrochemical Immunoassays:
2-Nitro-1-naphthol is used as a substrate in an amperometric 3-electrode system for the determination of alkaline phosphatase, the enzyme label most commonly used in electrochemical immunoassays.
Used in Chemical Synthesis:
2-Nitro-1-naphthol is used in the preparation of various compounds, including:
1. Di-(2-nitro-1-naphthyl) hydrogen phosphate: 2-Nitro-1-naphthol is used as a reagent in chemical synthesis.
2. 1-(2′-methyl-3′-indenyl)-2-naphthylamine: 2-Nitro-1-naphthol is used as an intermediate in the synthesis of pharmaceuticals and other organic compounds.
3. Axially chiral ligands: 2-Nitro-1-naphthol is used in the synthesis of axially chiral ligands, which are important in asymmetric catalysis and the development of enantioselective reactions.

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

• 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 
• 16155-58-1 2-p-tolyl-naphtho[2,1-d]oxazole 
• 70365-38-7 N-(1-hydroxynaphthalen-2-yl)acetamide 
• 20686-65-1 2-methyloxazolo<4,5-a>naphthalene 
• 697301-92-1 4-chloro-11-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentafuranosyl)-11H-benzo[e]pyrimido-[4,5-b]indole 
• 581-89-5 2-nitronaphthalene 
• 4185-55-1 1-bromo-2-nitro-naphthalene 
• 102154-23-4 1-iodo-2-nitronaphthalene 
• 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) 
• 861072-30-2 N-phenyl-1,2-diaminonaphthalene 

Relevant academic research and scientific papers

Photochemical reactions of diazodihydronaphthalenones in cyclic ethers

Photolysis of 4-diazonaphthalen-1(4H)-one (1a), 2-methyl-4-diazonaphthalen-1(4H)-one (1b) and 4-diazo-2-nitronaphthalen-1(4H)-one (1c) in neat THF and 1,4-dioxane produced a variety of products depending on the 2-substituent and the solvent. While 1a and

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.

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.

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.

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.

Room-Temperature, Water-Promoted, Radical-Coupling Reactions of Phenols with tert -Butyl Nitrite

A radical-radical cross-coupling reaction of phenols with tert -butyl nitrite has been developed with the use of water as an additive. This method allows the construction of C-N bonds under an air atmosphere at room temperature, providing the ortho -nitrated phenol derivative in moderate to good yields.

Tertiary Butyl Nitrite Triggered Nitration of Phenols: Solvent- and Structure-Dependent Kinetic Study

Nitration of phenols with tertiary butyl nitrite (TBN) obeyed second-order kinetics with a first-order dependence on [TBN] and [phenol] under acid-free conditions. Reaction rates were significantly altered by a change in the dielectric constant and other physical properties of solvent. The rate of nitration increased with an increase in temperature (303-323 K) in different solvent media (acetonitrile, dichloroethane, CCl4, dimethyl formamide (DMF), and toluene). The rates of nitration (log k) could not fit into either Amis or Kirkwood plots [log k' vs. (1/D) or [(D - 1)/(2D + 1)], but the trends were better explained by the basic form of multivariate linear solvent energy relationships (MLSER) suggested by the Koppel and Palm approach on the one hand and the Kamlet and Taft approach on the other hand. These observations probably substantiate that cumulative contributions of basic solvent parameters (equilibrium as well as frictional solvent effects) and solvent-solute interactions for solvation of transition state during nitration of phenols. Reaction rates accelerated with the introduction of electron-donating groups and retarded with electron-withdrawing groups. Accordingly, the reactivity of structurally different phenols was found to follow the following sequence: p-OH > p-MeO > p-Me > H > m-Me > p-Cl > p-Br > m-Cl > p-NO2 > m-OH. The results are interpreted by Hammett's theory of linear free energy relationship. The reaction constant (Hammett's ρ) is a measure of the sensitivity of the reaction toward the electronic effects of the substituent. The rho (ρ) values obtained from the present experiments are fairly large negative values (ρ CH3) versus σ? or, Es or combined Taft's relationship. However, Charton's MLRA of the log k with polar, resonance, steric, hydrophobicity, and molar refractivity showing a very good linear relationship was obtained. It is of interest to note that when log kexp values are correlated with log kcal a perfect linearity is obtained with a correlation coefficient of unity, indicating the consonance between experimental and calculated rate constants in the present work.

N-methyl-2-chloropyridinium iodide/NaNO2/Wet SiO2: Neutral reagent system for the nitration of activated aromatic compounds under very mild conditions

Mononitration of activated aromatic compounds using N-methyl-2-chloro-pyridinium iodide (Mukaiyama reagent)/NaNO2/wet SiO2 reagent system under neutral, very mild and environmentally safer reaction condition has been developed. Various structurally diverse aromatic rings are subjected in this condition and the corresponding nitro-aromatic compounds are prepared in moderately high yields.

Vanadium pentoxide as a catalyst for regioselective nitration of organic compounds under conventional and nonconventional conditions

Vanadium pentoxide is used as an efficient catalyst for regioselective nitration of aromatic compounds under conventional and nonconventional conditions such as ultrasonically assisted (USAR) and microwave-assisted reactions (MWAR). The reactions underwent smoothly and afforded good yields of products with high regioselectivity. Observed longer reaction times (about 8 h) in V2O5 catalyzed reactions reduced to (0.5/30 min) under sonication and (90 s) in the case of MWAR. When ortho position is blocked, para derivatives are obtained as end products while ortho nitro products are obtained when para position is blocked.