150-75-4

Usage

Uses

Used in Pharmaceutical Industry:
p-(methylamino)-pheno is used as a synthetic intermediate for the development of arylidene amino azolones, which possess anticancer activity. Its role in the synthesis of these compounds contributes to the fight against cancer by providing a chemical foundation for the creation of potential therapeutic agents.
Used in Cancer Research:
In the field of cancer research, p-(methylamino)-pheno is utilized to prepare N-(4-hydroxyphenyl)retinamide analogs. These analogs have demonstrated antitumor and apoptosis-inducing activities, making them valuable in the development of novel cancer treatments and therapies.
Overall, p-(methylamino)-pheno plays a significant role in the pharmaceutical and cancer research industries, serving as a key intermediate in the synthesis of compounds with potential therapeutic applications.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 43, p. 766, 1995 DOI: 10.1248/cpb.43.766

Contact allergens

Metol is contained in black and white film developers and caused contact dermatitis in photographers.

InChI:InChI=1/C7H9NO.H2O4S/c1-8-6-2-4-7(9)5-3-6;1-5(2,3)4/h2-5,8-9H,1H3;(H2,1,2,3,4)

Upstream product

• 106-41-2 4-bromo-phenol 
• 593-51-1 methylamine hydrochloride 
• 1693-39-6 N-(4-hydroxyphenyl)formamide 
• 122-87-2 N-(hydroxyphenyl)glycine 
• 123-30-8 4-amino-phenol 
• 512-42-5 sodium methyl sulfate 
• 106-48-9 4-chloro-phenol 
• 74-89-5 methylamine 
• 56-23-5 tetrachloromethane 
• 64-17-5 ethanol 
• 123-31-9 hydroquinone 
• 141-52-6 sodium ethanolate 
• 588-53-4 4-benzylidenamino-phenol 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 71045-92-6 N-[2-(4-hydroxy-N-methyl-anilino)-ethyl]-methanesulfonamide 
• 701-56-4 4-methoxy-N,N-dimethylanilne 
• 2142-04-3 2-(4-methoxyphenyl)isoindoline-1,3-dione 
• 3154-18-5 N-methyl-p-phenetidine 
• 42473-87-0 2-(4-ethoxyphenyl)isoindoline-1,3-dione 
• 67274-57-1 N-ethyl-N-methyl-p-phenetidine 
• 6062-24-4 1-methyl-5-hydroxy-2-indolinone 
• 106837-43-8 N-(4-hydroxy-phenyl)-N-methyl-urea 
• 2976-94-5 N-methyl-N-nitroso-4-hydroxyaniline 
• 70786-92-4 4-methylimino-cyclohexa-2,5-dienone 
• 106-51-4 p-benzoquinone 
• 74295-19-5 N-(4-acetato-phenyl)-N-methylacetamide 
• 855407-31-7 4-[(2-diethylamino-ethyl)-methyl-amino]-phenol 
• 6118-92-9 N-(4-hydroxy-phenyl)-N-methyl-glycine 

Relevant academic research and scientific papers

Commercial Pd/C-Catalyzed N-Methylation of Nitroarenes and Amines Using Methanol as Both C1 and H2 Source

Herein, we report commercially available carbon-supported-palladium (Pd/C)-catalyzed N-methylation of nitroarenes and amines using MeOH as both a C1 and a H2 source. This transformation proceeds with high atom-economy and in an environmentally friendly way via borrowing hydrogen mechanism. A total of >30 structurally diverse N-methylamines, including bioactive compounds, were selectively synthesized with isolated yields of up to 95%. Furthermore, selective N-methylation and deuteration of nimesulide, a nonsteroidal anti-inflammatory drug, were realized through the late-stage functionalization.

Highly Selective N-Monomethylanilines Synthesis from Nitroarene and Formaldehyde via Kinetically Excluding of the Thermodynamically Favorable N,N-Dimethylation Reaction

The synthesis of N-monomethylamine remains a challenging topic because the N,N-dimethylation reaction is thermodynamically favorable. In this work, the kinetically controlled N-monomethylamine synthesis from nitroarene and paraformaldehyde/H2 is reported to have superhigh N-monomethylamine selectivity in the presence of a Pd/TiO2 catalyst. The superior selectivity should be attributed to the preferential adsorption of the primary amine over N-monomethylamine on the Pd/TiO2 surface, as elucidated by NH3/Me2NH-TPD, while the excellent catalytic activity could be associated with the good H2 activation ability and high amine adsorbing capacity of the catalyst, as elucidated by NH3-TPD and H2-TPR tests. Good results were obtained with a variety of nitroarenes containing methyl, methoxyl, hydroxyl, fluoride, trifluoromethyl, ester, and amide substituents as starting materials, and the potential synthetic utility of this protocol in pharmaceutical is illustrated by N-monomethylation of drug molecules, such as clinidipine, nimesulide, procaine, and methyl aminosalicylate.

Method for selectively preparing N-monomethylamine compounds by using nitro compound as raw material

The invention discloses a method for selectively preparing N-monomethylamine compounds by using a nitro compound as a raw material. The method uses the nitro compound as the reaction raw material, formaldehyde as a methylating agent and a hydrogen gas as a reducing agent, in the presence of a supported type catalyst, a reaction is performed for 2-48 h at temperature of 10-180 DEG C in a reaction medium, and therefore the N-monomethylamine compounds are obtained, wherein the catalyst is at least one catalyst supported by palladium, platinum, ruthenium or rhodium. The method disclosed by the invention is simple, and can obtain the target product in a low-cost high-yield and high-selectivity manner; the method simplifies reaction steps, improves reaction efficiency, reduces reaction costs, and avoids separation of an intermediate product primary amine with high toxicity, easy deterioration and difficult storage; the method adopts the H2 as the reducing agent, thereby being clean, inexpensive and environmentally friendly; and the reaction conditions of the method are mild, and the catalyst is non-corrosive and easy to separate and reuse.

A series of BiO: XIy/GO photocatalysts: Synthesis, characterization, activity, and mechanism

A series of bismuth oxyiodide (BiOxIy)-grafted graphene oxide (GO) sheets with different GO contents were synthesized through a simple hydrothermal method. This is the first report where four composites of BiOI/GO, Bi4O5I2/GO, Bi7O9I3/GO, and Bi5O7I/GO have been characterized using X-ray diffraction, transmission electron microscopy, scanning electron microscopy energy-dispersive spectroscopy, Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, and diffuse reflectance spectroscopy. The assembled BiOxIy/GO composites exhibited excellent photocatalytic activities in the degradation of crystal violet (CV) under visible light irradiation. The order of rate constants was as follows: Bi7O9I3/GO > Bi4O5I2/GO > Bi4O5I2 > Bi7O9I3 > Bi5O7I/GO > BiOI/GO > BiOI > Bi5O7I > GO. The photocatalytic activity of the Bi7O9I3/GO (or Bi4O5I2/GO) composite reached a maximum rate constant of 0.351 (or 0.322) h-1, which was 1.8 (or 1.7) times higher than that of Bi7O9I3 (or Bi4O5I2), 6-7 times higher than that of BiOI/GO, and 119-130 times higher than that of BiOI. The quenching effects of different scavengers and electron paramagnetic resonance demonstrated that the superoxide radical (O2-) played a major role and holes (h+) and hydroxyl radicals (OH) played a minor role as active species in the degradation of crystal violet (CV) and salicylic acid (SA). Possible photodegradation mechanisms are proposed and discussed in this research.

N-Alkylation of Alkylolamines with Alcohols Over Mesoporous Solid Acid–Base Cs–B–Zr Catalyst

Abstract: The mesoporous solid acid–base Cs–B–Zr mixed oxides were synthesized using the co-precipitation method followed by a subsequent thermal treatment. The catalytic activity of solid Cs–B–Zr mixed oxide was tested for solvent free acid–base catalysed direct alkylolamines with alcohols as green alkylating agent. The effects of Cs/B/Zr ratio, calcination temperature, reaction conditions, and reaction substrate on the catalytic performance of the catalysts were investigated. The XRD, N2 adsorption–desorption, ICP-OES, FT-IR and NH3/CO2-TPD results showed that the mesoporous structure and acid–base properties of the catalysts play important roles in the reaction. A suitable number of acid and basic sites on the catalyst lead to a high activity for the N-alkylation reaction. Graphical Abstract: A direct N-alkylation of amino alcohol with alcohols has been developed using mixed oxide Cs–B–Zr as an acid–base bifunctionalized catalyst.[Figure not available: see fulltext.]

Room-temperature copper-catalyzed arylation of dimethylamine and methylamine in neat water

The first room-temperature copper-catalyzed arylations of dimethylamine and methylamine in neat water have been developed. Using a combination of CuI and 6,7-dihydroquinolin-8(5 H)-one oxime as catalyst, dimethylamine is arylated with various aryl halides to give the corresponding products in good to excellent yields. Further, this catalysis enables the selective arylation of methylamine to afford the high yields of monoarylated methylamines as the sole products.

A switchable [2]rotaxane asymmetric organocatalyst that utilizes an acyclic chiral secondary amine

A rotaxane-based switchable asymmetric organocatalyst has been synthesized in which the change of the position of the macrocycle reveals or conceals an acyclic, yet still highly effective, chiral organocatalytic group. This allows control over both the rate and stereochemical outcome of a catalyzed asymmetric Michael addition.

Demethylation of aromatic methyl ethers using ionic liquids under microwave irradiation

An efficient demethylation reaction for aromatic methyl ethers has been developed. Deprotection reactions give high yields with butylpyridinium bromide under microwave irradiation. Basic and acidic functional groups are tolerated if the reaction is performed under acidic conditions.

Layered double hydroxide-supported l-methionine-catalyzed chemoselective o-methylation of phenols and esterification of carboxylic acids with dimethyl carbonate: A "green" protocol

" Chemical equation presented" Simple methodology: A layered double hydroxide-supported L-methionine (LDH-Met) catalyst is designed in a simple methodology to explore its synthetic utility in biologically relevant reactions. The organocatalyst is characterized by FT-IR, TGA/DTA, powder XRD, and EDX spectroscopic techniques. This material has been successfully utilized for the preparation of aryl methyl ethers and esters from the corresponding phenols and carboxylic acids, respectively, in moderate to high yields (see scheme).

Fast deprotection of phenoxy benzyl ethers in transfer hydrogenation assisted by microwave

Phenoxy benzyl ethers are easily and quickly deprotected in the presence of ammonium formate and microencapsulated Pd(0)EnCat with the assistance of microwave irradiation. This procedure can be applied in the presence of other functional groups as well. The described protocol is particularly convenient for the preparation in a parallel and automatic fashion of libraries of compounds possessing a phenol type moiety.