150-75-4

Basic information

• Product Name: p-(methylamino)-pheno
• Synonyms: 4-(methylamino)phenol;4-(methylamino)phenol[qr];n-methyl-4-aminophenol;n-methyl-p-aminophenol[qr];p-(methylamino)-pheno;p-(methylamino)phenol[qr];phenol,4-(methylamino)-[qr];phenol,p-(methylamino)-[qr]
• CAS NO: 150-75-4
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15246
• EINECS: 205-768-2
• Mol File: 150-75-4.mol
• Article Data: 27

Chemical Properties

• Melting Point: 87 °C
• Boiling Point: 262.7 °C at 760 mmHg
• Flash Point: 148.6 °C
• Appearance: /
• Density: 1.147 g/cm³
• Vapor Pressure: 0.00658mmHg at 25°C
• PKA: 11.31±0.26(Predicted)
• CAS DataBase Reference: p-(methylamino)-pheno(CAS DataBase Reference)
• NIST Chemistry Reference: p-(methylamino)-pheno(150-75-4)
• EPA Substance Registry System: p-(methylamino)-pheno(150-75-4)

Safety Data

• RIDADR: 3077
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 150-75-4(Hazardous Substances Data)

Usage

Uses

4-Hydroxy-N-methylaniline is a useful synthetic intermediate. It is used to synthesize arylidene amino azolones with anticancer activity. It is also used to prepare N-(4-hydroxyphenyl)retinamide analogs with antitumor and apoptosis-inducing activities.

Definition

ChEBI: The phenol that is the N-methyl derivative of 4-aminophenol.

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 
• 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 
• 121-69-7 N,N-dimethyl-aniline 
• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 
• 7732-18-5 water 
• 75-52-5 nitromethane 

Downstream Products

• 6118-92-9 N-(4-hydroxy-phenyl)-N-methyl-glycine 
• 2567-80-8 chloro-acetic acid-(4-hydroxy-N-methyl-anilide) 
• 622-91-3 4-methylamino-phenol; compound of 4-methylamino-phenol with hydroquinone 
• 103501-59-3 N-(4-hydroxy-phenyl)-N-methyl-glycine amide 
• 3572-85-8 N-methanesulfonamido-N-methyl-4-hydroxyaniline 
• 619-60-3 4-(N,N-dimethylamino)phenol 
• 123-31-9 hydroquinone 
• 154286-48-3 C₇H₈NO 
• 120-80-9 benzene-1,2-diol 
• 100-22-1 N,N,N',N'-tetramethyl-para-phenylenediamine 
• 78711-50-9 4-[N-Methyl-N-(7-chloro-1,2,4-benzotriazin-3-yl)-amino]phenol 
• 106-51-4 p-benzoquinone 
• 320783-95-7 3-chloro-4-[4-(N-methylamino)phenoxy]benzonitrile 

Relevant articles and documents

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.

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.

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.]