99-53-6

Usage

Uses

Used in Environmental Analysis:
2-METHYL-4-NITROPHENOL is used as a target compound in the study on measurement of methylnitrophenol concentrations and stable isotope ratios in the atmospheric particulate matter. It helps in understanding the sources, transport, and fate of these compounds in the environment.
Used in Analytical Chemistry:
2-METHYL-4-NITROPHENOL is used as an internal standard in the determination of monoaromatic nitro compounds in atmospheric aerosols using high performance liquid chromatography electrospray tandem mass spectrometry (HPLC/ESI-MS/MS) method. It provides a reference point for accurate quantification and comparison of the target compounds.
Used in Organic Synthesis:
2-METHYL-4-NITROPHENOL may be used as a starting material in the synthesis of 2-bromo-4-nitro-6-methylphenol, which is an important intermediate in the production of various pharmaceuticals and agrochemicals.

InChI:InChI=1/C8H9NO3/c1-6-5-7(9(10)11)3-4-8(6)12-2/h3-5H,1-2H3

Upstream product

• 617-09-4 di-o-tolyl carbonate 
• 95-48-7 ortho-cresol 
• 455-88-9 5-nitro-2-fluorotoluene 
• 99-08-1 1-methyl-3-nitrobenzene 
• 636-21-5 o-toluidine hydrochloride 
• 7732-18-5 water 
• 95-53-4 o-toluidine 
• 7697-37-2 nitric acid 
• 71-43-2 benzene 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 7722-84-1 dihydrogen peroxide 
• 108-88-3 toluene 
• 13362-33-9 2-methyl-1,4-benzoquinone 4-oxime 

Downstream Products

• 67141-99-5 acetic acid 2-methyl-4-nitrophenyl ester 
• 60985-06-0 1-(1,1,2,3,3,3-Hexafluoro-propoxy)-2-methyl-4-nitro-benzene 
• 60984-98-7 1-(2-Chloro-1,1,2-trifluoro-ethoxy)-2-methyl-4-nitro-benzene 
• 50741-92-9 2-methyl-4-nitroanisole 
• 138227-68-6 1-tert-butyloxycarbonyl-4-(4-nitro-2methylphenyloxy)piperidine 
• 805238-45-3 (2-methyl-4-nitro-phenoxy)-acetic acid methyl ester 
• 630413-38-6 1-[(3-fluorobenzyl)oxy]-2-methyl-4-nitrobenzene 
• 148579-75-3 (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-methyl-4-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 83190-00-5 1-difluoromethoxy-2-methyl-4-nitrobenzene 
• 347161-73-3 6,7-dimethoxy-4-(2-methyl-4-nitrophenoxy)quinoline 
• 1099664-79-5 2-methyl-1-(2-methyl-4-nitrophenoxy)propan-2-ol 
• 1236764-21-8 1-(cyclopropylmethoxy)-2-methyl-4-nitrobenzene 
• 1239457-35-2 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-methyl-4-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1254579-58-2 C₁₁H₁₃NO₃ 

Relevant academic research and scientific papers

Aryl phenol compound as well as synthesis method and application thereof

The invention discloses a synthesis method of an aryl phenol compound shown as a formula (3). All systems are carried out in an air or nitrogen atmosphere, and visible light is utilized to excite a photosensitizer for catalyzation. In a reaction solvent, ArNR1R2 as shown in a formula (1) and water as shown in a formula (2) are used as reaction raw materials and react under the auxiliary action of acid to obtain the aryl phenol compound as shown in a formula (3). The ArNR1R2 in the formula (1) can be primary amine and tertiary amine, can also be steroid and amino acid derivatives, and can also be drugs or derivatives of propofol, paracetamol, ibuprofen, oxaprozin, indomethacin and the like. The synthesis method has the advantages of cheap and easily available raw materials, simple reaction operation, mild reaction conditions, high reaction yield and good compatibility of substrate functional groups. The fluid reaction not only can realize amplification of basic chemicals, but also can realize amplification of fine chemicals, such as synthesis of drugs propofol and paracetamol. The invention has wide application prospect and use value.

Kinetics and mechanism of trichloroisocyanuric acid/NaNO2-triggered nitration of aromatic compounds under acid-free and Vilsmeier-Haack conditions

Kinetics and mechanism of nitration of aromatic compounds using trichloroisocyanuric acid (TCCA)/NaNO2, TCCA-N,N-dimethyl formamide (TCCA-DMF)/NaNO2, and TCCA-N,N-dimethyl acetamide (TCCA-DMA)/NaNO2 under acid-free and Vilsmeier-Haack conditions. Reactions followed second-order kinetics with a first-order dependence on [Phenol] and [Nitrating agent] ([TCCA], [(TCCA-DMF)], or [(TCCA-DMA)] >> [NaNO2]). Reaction rates accelerated with the introduction of electron-donating groups and retarded with electron-withdrawing groups, but did not fit well into the Hammett's theory of linear free energy relationship or its modified forms like Brown-Okamoto or Yukawa-Tsuno equations. Rate data were analyzed by Charton's multiple linear regression analysis. Isokinetic temperature (β) values, obtained from Exner's theory for different protocols, are 403.7?K (TCCA-NaNO2), 365.8?K (TCCA-DMF)/NaNO2, and 358?K (TCCA-DMA)/NaNO2. These values are far above the experimental temperature range (303-323?K), indicating that the enthalpy factors are probably more important in controlling the reaction.

Silica-supported perchloric acid and potassium bisulfate as reusable green catalysts for nitration of aromatics under solvent-free microwave conditions

Silica-supported perchloric acid and bisulfate (SiO2/HClO4 and SiO2/KHSO4) have been developed as reusable green catalysts for nitration of aromatic compounds using NaNO2 in acetonitrile medium under conventional and solvent-free microwave conditions. The reaction times under microwave irradiation are significantly shorter than conventional method even though the yields obtained in microwave-assisted reactions are comparable with those obtained under reflux conditions.

Sodium perborate/NaNO2/KHSO4-triggered synthesis and kinetics of nitration of aromatic compounds

Sodium perborate (SPB) was used as efficient green catalyst for NaNO2/KHSO4-mediated nitration of aromatic compounds in aqueous acetonitrile medium. Synthesis of nitroaromatic compounds was achieved under both conventional and solvent-free microwave conditions. Reaction times were comparatively shorter in the microwave-assisted than conventional reaction. The reaction kinetics for nitration of phenols in aqueous bisulfate and acetonitrile medium indicated first-order dependence on [Phenol], [NaNO2], and [SPB]. Reaction rates accelerated with introduction of electron-donating groups but retarded with electron-withdrawing groups. Kinetic results did not fit well quantitatively with Hammett’s equation. Observed deviations from linearity were addressed in terms of exalted Hammett’s constants (σˉ or σeff), para resonance interaction energy (ΔΔGp) parameter, and Yukawa–Tsuno parameter (r). This term provides a measure of the extent of resonance stabilization for a reactive structure that builds up charge (positive) in its transition state. The observed negative entropy of activation (?ΔS#) suggests greater solvation and/or cyclic transition state before yielding products.

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.

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.

Synthesis method of 2-amino-4-chloro-6-metoxyphenol

The invention discloses a synthesis method of 2-amino-4-chloro-6-metoxyphenol, which belongs to the field of chemical synthesis. The method comprises the following steps of adding p-nitrophenol of nitrosonitric acid and sulfuric acid into phenol, adding methane chloride and anhydrous glacial acetic acid to obtain a mixture, then putting the mixture into a high-pressure autoclave, adding absolute ethyl alcohol and inputting hydrogen, performing pumping filtration to obtain filter residues after reaction, adding copper chloride into the filter residues, generating light green precipitation after adjusting pH through sodium hydroxide, filtering, washing the filter residues and drying to obtain the 2-amino-4-chloro-6-metoxyphenol.

A process for the preparation of nitro-O-cresol (by machine translation)

The invention discloses a method for the preparation of nitro-O-cresol, this method, in order to P-O-toluidine as raw material prepared by alkali hydrolysis of the nitro-O-cresol. The obtained P-O-cresol has high purity, measured by high-performance liquid chromatography (HPLC), area of quantitative normalization measured content of greater than 99%, yield is greater than 95%, the preparation method is simple and convenient to operate, in the method under the process conditions, repeat the plurality of batches, repeatability is good. (by machine translation)

Regioselective nitration of phenols and phenyl ethers using aluminium nitrate on silica as a nitrating system

Silica supported aluminum nitrate (Al(NO3)3·9H2O) was found to be an excellent reagent for the nitration of phenols and phenyl ethers. This procedure works efficiently on most of the examples at room temperature yielding nitro derivatives in fair to good yields with high regioselectivity. The present methodology evidenced a considerable enhancement in the reaction rate along with high o-selectivity, excellent yields, ease of handling and the simplicity in work up.