700-38-9

Usage

Uses

Used in Pharmaceutical Industry:
5-Methyl-2-nitrophenol is used as a chemical reagent for the synthesis of antifungal benzoxazine-3-4(H)-one derivatives. It plays a crucial role in the development of new antifungal agents to combat fungal infections.
Used in Levofloxacin Preparation:
5-Methyl-2-nitrophenol is also utilized in the preparation of Levofloxacin precursors. Levofloxacin is a widely used fluoroquinolone antibiotic, and 5-Methyl-2-nitrophenol serves as an essential intermediate in its production process.
Used in Organic Synthesis:
In the field of organic synthesis, 5-Methyl-2-nitrophenol was used in the synthesis of 3-methoxy-4-nitrotoluene. This application highlights its versatility as a reagent in creating various organic compounds for different industries.

InChI:InChI=1/C7H7NO3/c1-5-2-3-6(8(10)11)7(9)4-5/h2-4,9H,1H3/p-1

Upstream product

• 50-85-1 2-hydroxy-p-toluic acid 
• 62351-45-5 5-hydroxy-4-nitro-toluene-2-sulfonic acid 
• 591-09-3 nitro acetate 
• 108-24-7 acetic anhydride 
• 108-39-4 3-methyl-phenol 
• 99-87-6 4-methylisopropylbenzene 
• 4920-77-8 3-methyl-2-nitrophenol 
• 38512-82-2 3-methoxy-4-nitrotoluene 
• 563-04-2 tri-m-cresyl phosphate 
• 24542-06-1 5-methyl-2-nitrosophenol 
• 67-56-1 methanol 
• 7697-37-2 nitric acid 
• 71-43-2 benzene 
• 67-66-3 chloroform 

Downstream Products

• 38512-82-2 3-methoxy-4-nitrotoluene 
• 6623-41-2 2-amino-4,5-dimethylphenol 
• 23363-74-8 5,6-dimethyl-2-aminophenol 
• 869944-70-7 (5-methyl-2-nitro-phenoxy)-acetic acid 
• 619-14-7 3-hydroxy-4-nitro-benzoic acid 
• 616-73-9 4,6-dinitro-3-hydroxytoluene 
• 182500-28-3 4-bromo-5-methyl-2-nitrophenol 
• 7147-89-9 4-chloro-5-methyl-2-nitrophenol 
• 62351-45-5 5-hydroxy-4-nitro-toluene-2-sulfonic acid 
• 859937-37-4 2,4-dibromo-3-methyl-6-nitro-phenol 
• 856180-62-6 4-nitro-benzoic acid-(5-methyl-2-nitro-phenyl ester) 
• 2835-98-5 2-Hydroxy-4-methylanilin 
• 182913-38-8 5-methyl-2-nitrophenyl acetate 
• 127396-66-1 5-methyl-2-nitro-4,6-bis(pyrrolidin-1'-ylmethyl)phenol 

Relevant academic research and scientific papers

3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature

Due to their remarkable properties, task-specific ionic liquids have turned out to be progressively popular over the last few years in the field of green organic synthesis. Herein, for the first time, we report that a new task-specific nitrite-based ionic liquid such as 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imides (TS-N-IL) derived from biodegradable ethyl nicotinate indeed acted as an efficient and eco-friendly reagent for the synthesis of highly valuable nitroaromatic compounds and drugs including nitroxynil, tolcapone, niclofolan, flutamide, niclosamide and nitrazepam. The bridging of an ionic liquid with nitrite group not only increases the yield and rate of direct C[sbnd]N bond formation reaction but also allows easy product separation and recyclability of a byproduct. Nonvolatile nature, easy synthesis, merely stoichiometric need and mildness are a portion of the extra focal points of TS-N-IL while contrasted with tert-butyl nitrite an outstanding and highly-flammable reagent utilized largely in organic synthesis.

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.

3-Hydroxyl-4-nitrobenzoic acid and preparation method thereof

The invention aims to provide 3-hydroxyl-4-nitrobenzoic acid and a preparation method thereof. The preparation method includes: subjecting low-price and easily obtainable m-cresol as a raw material to nitration and then oxidation; with H2O2 serving as an oxidant, oxidizing a methyl group into a carboxyl group so as to obtain 3-hydroxyl-4-nitrobenzoic acid. The method has the advantages of low material cost, operation simplicity, low byproduct output, high yield and mild reaction environmental conditions and is suitable for large-scale industrial production.

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.

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.

Cyclodextrin-based artificial oxidases with high rate accelerations and selectivity

Three cyclodextrin derivatives with one to four 2-O-formylmethyl groups attached to the secondary rim were prepared and investigated as catalysts for the oxidation of aminophenols in buffered dilute hydrogen peroxide. The derivatives were found to be Michaelis-Menten catalysts and to give rate accelerations of up to 20,000 for the oxidation of 2-aminophenol to 2-amino-phenoxazin-3-one, and 12,000 for the oxidation of 2-amino-p-cresol to 2-nitro-p-cresol. While a range of differently substituted substrates was oxidized the success of the reaction was highly dependent on the substituent pattern. The ability of one of the new artificial enzymes to oxidize selectively one aminophenol from a mixture of two was investigated giving substrate selectivities of up to 16:1.

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.

Ultrasonic and microwave-assisted synthesis of β-nitro styrenes and nitro phenols with tertiary butyl nitrite under acid-free conditions

Tertiary butyl nitrite (TBN) is an acid-free and safe nitrating agent that provides preferentially β-nitrostyrenes with cinnamic acids and corresponding nitro derivatives with phenols in good yields under classical conditions. However, ultrasonic and microwave-assisted reactions reduced the reaction times substantially and enhanced the yields from good to excellent. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

A tandem reduction-oxidation protocol for the conversion of 1-keto-1,2,3,4-tetrahydrocarbazoles to carbazoles via tosylhydrazones through microwave assistance: Efficient synthesis of glycozoline, clausenalene, glycozolicine, and deoxycarbazomycin B and the total synthesis of murrayafoline A

A novel and efficient methodology for the synthesis of carbazoles from 1-keto-1,2,3,4-tetrahydrocarbazoles via the corresponding tosylsulfonhydrazones by a one-pot tandem reduction-oxidation protocol using a combination of NaBH4 and Pd-C on MgSO4·7H2O, a solid support, under microwave is developed. The reaction is successfully extended toward the synthesis of several naturally occurring carbazole alkaloids, namely 3-methylcarbazole, glycozoline, clausenalene, glycozolicine, murrayafoline A, and deoxycarbazomycin B, a carbazole derivative that is known to have a promising antimicrobial activity.

Cellulose-supported Ni(NO3)2.6H2O/2,4,6- trichloro-1,3,5-triazine (TCT) as a mild, selective, and biodegradable system for nitration of phenols

Nitration of certain phenols and naphthols in the presence of biodegradable cellulose-supported Ni(NO3)2.6H2O/2,4,6- trichloro-1,3,5-triazine was carried out in acetonitrile at room temperature. Ortho nitrated phenols were obtained regioselectively within a short reaction time with good yields. The reaction condition was mild, and the employed cellulose could be recovered several times for further use. Copyright