101-64-4

Basic information

• Product Name: 4-Amino-4'-methoxydiphenylamine
• Synonyms: n-(4-methoxyphenyl)-4-benzenediamine;N-(4-METHOXYPHENYL)-1,4-PHENYLENEDIAMINE;VARIAMINE BLUE B BASE;ASISCHEM D50974;AURORA KA-7508;4-AMINO-4'-METHOXYDIPHENYLAMINE;N-(4-aminophenyl)-p-anisidine;VARIAMINE BLUE B BASE [REDOX INDICATOR]
• CAS NO: 101-64-4
• Molecular Formula: C₁₃H₁₄N₂O
• Molecular Weight: 214.26
• EINECS: 202-962-9
• Mol File: 101-64-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 101°C
• Boiling Point: 210 °C / 4mmHg
• Flash Point: 188.9°C
• Appearance: /
• Density: 1.0850 (rough estimate)
• Vapor Pressure: 3.01E-06mmHg at 25°C
• Refractive Index: 1.6450 (estimate)
• Merck: 14,5999
• CAS DataBase Reference: 4-Amino-4'-methoxydiphenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-4'-methoxydiphenylamine(101-64-4)
• EPA Substance Registry System: 4-Amino-4'-methoxydiphenylamine(101-64-4)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2811
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 101-64-4(Hazardous Substances Data)

Usage

General Description

4-Amino-4'-methoxydiphenylamine is characterized by its structure, which includes a diphenylamine core with an amino group (-NH2) at the 4-position of one phenyl ring and a methoxy group (-OCH3) at the 4'-position of the other phenyl ring. It is commonly employed in the production of dyes, particularly in the synthesis of azo dyes, where its amino group can undergo diazo coupling reactions with other aromatic compounds to create a wide range of colorful dye molecules. Its role as a dye intermediate makes it important in the textile, ink, and pigment industries, contributing to the vibrant colors seen in various products.

Purification Methods

Crystallise the diamine from ligroin or *C6H6/pet ether (m 99-100o). The picrate has m 164o (from EtOH). [Beilstein 13 III 1161, 13 IV 1243.]

InChI:InChI=1/C13H14N2O/c1-16-13-8-6-12(7-9-13)15-11-4-2-10(14)3-5-11/h2-9,15H,14H2,1H3

Upstream product

• 100-17-4 para-methoxynitrobenzene 
• 62-53-3 aniline 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 967-35-1 N-(4-methoxyphenyl)-2,4-dinitrobenzenamine 
• 41018-73-9 4-chloro-N-(4-methoxyphenyl)aniline 
• 2101-87-3 p-methoxy-phenylazide 
• 104-94-9 4-methoxy-aniline 
• 586-78-7 para-nitrophenyl bromide 
• 623-12-1 4-chloromethoxybenzene 
• 106-50-3 1,4-phenylenediamine 
• 1208-86-2 N-(4-methoxyphenyl)phenylamine 
• 41018-65-9 (4-methoxy-phenyl)-nitroso-phenyl-amine 
• 63235-31-4 benzenesulfenic acid p-anisidide 

Downstream Products

• 33840-14-1 [1,4]benzoquinone-imine-(4-methoxy-phenylimine) 
• 101677-23-0 3-amino-2,4,6,8-tetrachloro-7-methoxy-phenothiazinylium; chloride 
• 27163-30-0 4-Methoxy-4'-isothiocyano-diphenylamin 
• 43096-14-6 N-{4-[4-(4-Methoxy-phenylamino)-phenylamino]-9,10-dioxo-9,10-dihydro-anthracen-1-yl}-benzamide 
• 54480-44-3 N,N-dimethyl-N'-(4-methoxyphenyl)-1,4-phenylendiamine 
• 118739-43-8 N,N,N-trimethyl-N'-(4-methoxyphenyl)-1,4-phenylendiamine 
• 55872-66-7 4-(benzoylamino)-4'-methoxydiphenylamine 
• 54536-23-1 1-(methoxy-d₃)-4-nitrobenzene 
• 4019-64-1 N,N-dimethyl-4-trideuteriomethoxy-aniline 
• 180626-23-7 4-([D₃]methoxy)aniline 
• 350-46-9 4-Fluoronitrobenzene 
• 102316-47-2 N-benzyl-N'-(4-methoxy-phenyl)-p-phenylenediamine 
• 67979-39-9 4-((4-methoxyphenyl)imino)cyclohexa-2,5-dien-1-one 
• 225381-91-9 N-(4-Methoxy-phenyl)-N'-thieno[3,2-d]pyrimidin-4-yl-benzene-1,4-diamine 

Relevant articles and documents

Efficient and Selective Oxidation of Aromatic Amines to Azoxy Derivatives over Aluminium and Gallium Oxide Catalysts with Nanorod Morphology

Aluminium oxide and gallium oxide nanorods were identified as highly efficient heterogeneous catalysts for the selective oxidation of aromatic amines to azoxy compounds using hydrogen peroxide as environmentally friendly oxidant. This is the first report of the selective oxidation of aromatic amines to their azoxy derivatives without using transition metal catalysts. Among the tested transition-metal-free oxides, gallium oxide nanorods with small dimensions (9–52 nm length and 3–5 nm width) and fully accessible, high surface area (225 m2 g?1) displayed the best catalytic performance in terms of substrate versatility, activity and azoxybenzene selectivity. Furthermore, the catalyst loading, hydrogen peroxide type (aqueous or anhydrous), and the amount of solvent were tuned to optimise the catalytic performance, which allowed reaching almost full selectivity (98 %) towards azoxybenzene at high aniline conversion (94 %). Reusability tests showed that the gallium oxide nanorod catalyst can be recycled in consecutive runs with complete retention of the original activity and selectivity.

Discovery of a novel small-molecule inhibitor of Fam20C that induces apoptosis and inhibits migration in triple negative breast cancer

The family with sequence similarity 20, member C (Fam20C), a Golgi casein kinase, has been recently regarded as a potential therapeutic target for the treatment of triple negative breast cancer (TNBC). Lacking enzyme activity center has been becoming an obstacle to the development of small-molecule inhibitors of Fam20C. Herein, we combined in silico high-throughput screening with chemical synthesis methods to obtain a new small-molecule Fam20C inhibitor 3r, which exhibited desired anti-proliferative activities against MDA-MB-231 cells and also inhibited migration. Subsequently, the enzymatic assay, molecular docking, and molecular dynamics (MD) simulations were carried out for validating that 3r could bind to Fam20C. In addition, 3r was found to induce apoptosis via the mitochondrial pathway in MDA-MB-231 cells as well as to inhibit cell migration. Moreover, we demonstrated that 3r inhibited tumor growth in vivo and thereby having a good therapeutic potential on TNBC. Taken together, these results suggest that 3r may be a novel Fam20C inhibitor with anti-proliferative and apoptosis-inducing activities, which would shed light on discovering more small-molecule drugs for the future TNBC therapy.

NOVEL CATALYSTS

The present invention provides novel compounds and ligands that are useful in transition metal catalyzed cross-coupling reactions. For example, the compounds and ligands of the present invention are useful in palladium or gold catalyzed cross-coupling reactions.