99-53-6

Basic information

• Product Name: 2-METHYL-4-NITROPHENOL
• Synonyms: 2-HYDROXY-5-NITROTOLUENE;2-METHYL-4-NITROPHENOL;4-NITRO-O-CRESOL;4-nitro-o-creso;Phenol, 2-methyl-4-nitro-;4-NITRO-2-CRESOL;4-Nitro-o-cresol (OH=1);2-METHYL-4-NITROPHENOL (4-NITRO-O-CRESOL)
• CAS NO: 99-53-6
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.14
• EINECS: 202-763-7
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Phenoles and thiophenoles;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 99-53-6.mol
• Article Data: 45

Chemical Properties

• Melting Point: 93-98 °C(lit.)
• Boiling Point: 266.03°C (rough estimate)
• Flash Point: 143.1 °C
• Appearance: /
• Density: 1.2744 (estimate)
• Vapor Pressure: 0.00556mmHg at 25°C
• Refractive Index: 1.5744 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.43±0.22(Predicted)
• CAS DataBase Reference: 2-METHYL-4-NITROPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-4-NITROPHENOL(99-53-6)
• EPA Substance Registry System: 2-METHYL-4-NITROPHENOL(99-53-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 2446 6.1/PG 3
• WGK Germany: 3
• RTECS: GP2700000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 99-53-6(Hazardous Substances Data)

Usage

Chemical Properties

white crystals

Uses

2-Methyl-4-nitrophenol is suitable as a target compound in the study on measurement of methylnitrophenol concentrations and stable isotope ratios in the atmospheric particulate matter and 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 may be used as starting material in the synthesis of 2-bromo-4-nitro-6-methylphenol.

General Description

2-Methyl-4-nitrophenol is a nitrophenol derivative. The study of its crystal structure reveals the molecule to be nearly planar. Its synthesis has been reported. FT-IR and FT-Raman spectra and molecular modeling of 2-methyl-4-nitrophenol have been analyzed. It is reported to be one of the compounds in diesel exhaust particles (DEP) that shows potential vasodilatation activity in rats. Its reduction catalyzed by porous carbon-encapsulated gold nanoparticles has been investigated.

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

Upstream product

• 110-89-4 piperidine 
• 50741-92-9 2-methyl-4-nitroanisole 
• 6971-38-6 p-nitroso-o-cresol 
• 617-09-4 di-o-tolyl carbonate 
• 636-21-5 o-toluidine hydrochloride 
• 95-48-7 ortho-cresol 
• 95-53-4 o-toluidine 
• 99-52-5 2-methyl-4-nitro-benzenamine 
• 455-88-9 5-nitro-2-fluorotoluene 
• 99-08-1 1-methyl-3-nitrobenzene 
• 7732-18-5 water 
• 7697-37-2 nitric acid 
• 71-43-2 benzene 
• 64-19-7 acetic acid 

Downstream Products

• 2835-96-3 4-amino-2-methylphenol 
• 4186-49-6 2-bromo-6-methyl-4-nitrophenol 
• 117043-13-7 dichlorophosphoric acid-(2-methyl-4-nitro-phenyl ester) 
• 50741-92-9 2-methyl-4-nitroanisole 
• 955369-16-1 dimethyl{2-[(2-methyl-4-nitrophenyl)oxy]ethyl}amine 
• 871020-31-4 2-(2-methyl-4-nitrophenoxy)pyrazine 
• 871020-24-5 2-(2-methyl-4-nitrophenoxy)pyridine 
• 864244-98-4 4-(2-methyl-4-nitrophenoxy)pyridin-2-amine 
• 630413-38-6 1-[(3-fluorobenzyl)oxy]-2-methyl-4-nitrobenzene 
• 138227-68-6 1-tert-butyloxycarbonyl-4-(4-nitro-2methylphenyloxy)piperidine 
• 83190-00-5 1-difluoromethoxy-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 
• 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 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.

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.

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.