2042-14-0

Basic information

• Product Name: 4-Methyl-3-nitrophenol
• Synonyms: 2-Nitro-4-hydroxytoluene;3-Nitro-p-cresol(4-Methyl-3-nitrophenol);p-Cresol, 3-nitro-;Phenol, 4-methyl-3-nitro-;4-HYDROXY-1-METHYL-2-NITROBENZENE;4-HYDROXY-2-NITROTOLUENE;4-METHYL-3-NITROPHENOL;3-NITRO-P-CRESOL
• CAS NO: 2042-14-0
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.14
• EINECS: 218-044-6
• Product Categories: Intermediates of Dyes and Pigments;Aromatic Phenols;Phenoles and thiophenoles;Aromatics Compounds;Naphthyridine,Quinoline;Aromatics;Pyrimidines
• Mol File: 2042-14-0.mol

Chemical Properties

• Melting Point: 78-81 °C
• Boiling Point: 266.03°C (rough estimate)
• Flash Point: 125.2 °C
• Appearance: /Powder
• Density: 1.2744 (estimate)
• Vapor Pressure: 0.00294mmHg at 25°C
• Refractive Index: 1.5744 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Ethyl Acetate, Methanol
• PKA: 8.66±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 4-Methyl-3-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methyl-3-nitrophenol(2042-14-0)
• EPA Substance Registry System: 4-Methyl-3-nitrophenol(2042-14-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36
• RIDADR: 2446
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2042-14-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Methyl-3-nitrophenol is used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure allows it to be a versatile building block in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Methyl-3-nitrophenol is used as a key intermediate in the synthesis of certain drugs. Its presence in the molecular structure can impart specific biological activities, making it an essential component in the development of new medications.
Used in Agrochemical Industry:
4-Methyl-3-nitrophenol is also utilized in the agrochemical industry for the production of pesticides and other crop protection agents. Its chemical properties enable it to be incorporated into formulations that effectively control pests and diseases in agriculture.
Used in Specialty Chemicals:
In the specialty chemicals sector, 4-Methyl-3-nitrophenol is employed in the development of dyes, pigments, and other colorants. Its ability to impart color and stability to various materials makes it a valuable component in the creation of high-quality products.

Synthesis Reference(s)

Synthesis, p. 735, 1986 DOI: 10.1055/s-1986-31759

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

Upstream product

• 119-32-4 4-Methyl-3-nitroanilin 
• 106-38-7 para-bromotoluene 
• 7664-93-9 sulfuric acid 
• 621-02-3 di-p-tolyl carbonate 
• 7697-37-2 nitric acid 
• 80500-27-2 (4-methyl-3-nitrophenyl)boronic acid 
• 16296-53-0 4-methyl-3-nitrophenyl methanesulfonate 
• 106-44-5 p-cresol 
• 64-19-7 acetic acid 
• 50343-63-0 carbonic acid bis-(4-methyl-3-nitro-phenyl ester) 

Downstream Products

• 859198-73-5 4-methyl-2-(4-methyl-3-nitro-phenoxy)-quinoline 
• 102871-92-1 4-ethoxy-1-methyl-2-nitrobenzene 
• 858451-94-2 2-methyl-4-(4-methyl-3-nitro-phenoxy)-quinoline 
• 24239-67-6 4-(benzyloxy)-1-methyl-2-nitrobenzene 
• 100725-89-1 benzoic acid-(4-methyl-3-nitro-phenyl ester) 
• 17484-36-5 4-Methyl-3-nitroanisole 
• 38524-64-0 Thiophosphoric acid O-ethyl ester O'-(4-methyl-3-nitro-phenyl) ester S-propyl ester 
• 27077-78-7 4-methyl-2,3-dinitroanisole 
• 112251-86-2 4-methyl-3,4-dinitrocyclohexa-2,5-dienone 
• 112251-94-2 (Z)-3-methoxy-6-methyl-5,6-dinitrocyclohexa-2,4-dienyl acetate 
• 41447-19-2 1-bromo-2-methoxy-5-methyl-4-nitrobenzene 
• 860734-28-7 2-bromo-1-methoxy-4-methyl-3-nitrobenzene 
• 92238-16-9 acetic acid-(2-bromo-4-methyl-5-nitro-phenyl ester) 
• 50868-72-9 5-methoxy-o-toluidine 

Relevant articles and documents

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.

DDX3X inhibitors, an effective way to overcome HIV-1 resistance targeting host proteins

The huge resources that had gone into Human Immunodeficiency virus (HIV) research led to the development of potent antivirals able to suppress viral load in the majority of treated patients, thus dramatically increasing the life expectancy of people living with HIV. However, life-long treatments could result in the emergence of drug-resistant viruses that can progressively reduce the number of therapeutic options, facilitating the progression of the disease. In this scenario, we previously demonstrated that inhibitors of the human DDX3X helicase can represent an innovative approach for the simultaneous treatment of HIV and other viral infections such as Hepatitis c virus (HCV). We reported herein 6b, a novel DDX3X inhibitor that thanks to its distinct target of action is effective against HIV-1 strains resistant to currently approved drugs. Its improved in vitro ADME properties allowed us to perform preliminary in vivo studies in mice, which highlighted optimal biocompatibility and an improved bioavailability. These results represent a significant advancement in the development of DDX3X inhibitors as a novel class of broad spectrum and safe anti-HIV-1 drugs.

The highly efficient air oxidation of aryl and alkyl boronic acids by a microwave-assisted protocol under transition metal-free conditions

Molecular oxygen is the most important green-oxidant due to its excellent properties. However, the effective utilization of molecular oxygen remains a major challenge in modern chemistry. Herein, we report the development a rapid, green and efficient microwave-assisted protocol for the air oxidation of boronic acids to phenols and alcohols under transition metal-free conditions. In the presence of KOH and DMSO, high yields of the expected phenols and alcohol were obtained with microwave-assistance, and a variety of functional groups were tolerated in this procedure. Notably, this transition metal-free method represents a breakthrough in both organic synthesis and green chemistry for the oxidative hydroxylation of boronic acids to phenols and alcohols.

Cell-Based Optimization of Covalent Reversible Ketoamide Inhibitors Bridging the Unprimed to the Primed Site of the Proteasome β5 Subunit

The ubiquitin-proteasome system (UPS) is an established therapeutic target for approved drugs to treat selected hematologic malignancies. While drug discovery targeting the UPS focuses on irreversibly binding epoxyketones and slowly-reversibly binding boronates, optimization of novel covalent-reversibly binding warheads remains largely unattended. We previously reported α-ketoamides to be a promising reversible lead motif, yet the cytotoxic activity required further optimization. This work focuses on the lead optimization of phenoxy-substituted α-ketoamides combining the structure-activity relationships from the primed and the non-primed site of the proteasome β5 subunit. Our optimization strategy is accompanied by molecular modeling, suggesting occupation of P1′ by a 3-phenoxy group to increase β5 inhibition and cytotoxic activity in leukemia cell lines. Key compounds were further profiled for time-dependent inhibition of cellular substrate conversion. Furthermore, the α-ketoamide lead structure 27 does not affect escape response behavior in Danio rerio embryos, in contrast to bortezomib, which suggests increased target specificity.

USE OF DDX3 INHIBITORS AS ANTIPROLIFERATIVE AGENTS

The present invention refers to compounds of formula I or II endowed with DDX3 inhibitory activity, relative pharmaceutical compositions and their use as antihyperproliferative agents. (I) or (II)

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.

HUMAN HELICASE DDX3 INHIBITORS AS THERAPEUTIC AGENTS

The present invention refers to compounds endowed with RNA helicase DDX3 inhibitory activity of formula I and II and their therapeutic use, in particular for the treatment of viral diseases.

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.

Fast and efficient nitration of salicylic acid and some other aromatic compounds over H3PO4/TiO2-ZrO2 using nitric acid

TiO2-ZrO2 (1/1)-surf with Ti and Zr molar ratio of 1/1 was prepared with surfactant through a sol-gel method. The optimum experimental condition was investigated for nitration of salicylic acid. Then, a number of nitration reactions were carried out with a variety of aromatic compounds in the optimum condition. The 25 wt% H3PO4/TiO2-ZrO2 (1/1)-surf catalyst showed good selectivity and yield in a short time for the nitration of salicylic acid and some other aromatic compounds.

Catalytic asymmetric intramolecular hydroarylations of ω-aryloxy- and arylamino-tethered α,β-unsaturated aldehydes

The first enantioselective organocatalytic intramolecular hydroarylations of phenol and aniline-derived enals were investigated. The proposed method provided an atom economic and straightforward approach to optically active chromans and tetrahydroquinolines in high enantioselectivities and in good yields. The study demonstrated the efficiency of organocatalysis to achieve the first asymmetric intramolecular arylation of ω aryloxy- arylamino-tethered α, and β-unsaturated aldehydes using a chiral secondary amine catalyst. Proposed transformation method resulted in the production of functionalized chromans and tetrahydroquinoline in high enantiopurity. The study also examined the scope of substrates in this organocatalytic reaction using a catalyst 4/p-TsOH.H2O in diethyl ether. The catalyst screening observed a higher yield up to 83% and comparable enantiometric excess up to 88% that can be obtained in a chiral secondary amine employed as the reaction catalyst.