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

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

Uses

Used in Textile Industry:
VARIAMINE BLUE B BASE is used as a dye intermediate for the synthesis of azo dyes, which are important for coloring fabrics and textiles. Its role in creating a wide range of vibrant colors contributes to the aesthetic appeal and variety of textile products.
Used in Ink Industry:
In the ink industry, VARIAMINE BLUE B BASE is used as a dye intermediate to produce azo dyes that impart color to various types of inks, including printing inks and writing inks. Its ability to create a diverse palette of colors is essential for the production of high-quality inks with consistent color properties.
Used in Pigment Industry:
VARIAMINE BLUE B BASE is utilized as a dye intermediate in the synthesis of azo pigments, which are used in various applications such as paints, coatings, and plastics. Its contribution to the creation of a broad spectrum of colors is crucial for the development of pigments with specific color characteristics and performance properties.

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

• 7647-01-0 hydrogenchloride 
• 33836-66-7 5-amino-2-p-anisidino-benzenesulfonic acid 
• 623-12-1 4-chloromethoxybenzene 
• 106-50-3 1,4-phenylenediamine 
• 104-94-9 4-methoxy-aniline 
• 586-78-7 para-nitrophenyl bromide 
• 350-46-9 4-Fluoronitrobenzene 
• 123-30-8 4-amino-phenol 
• 16078-86-7 4-Hydroxy-4'-nitrodiphenylamine 
• 2101-87-3 p-methoxy-phenylazide 
• 41018-73-9 4-chloro-N-(4-methoxyphenyl)aniline 
• 122-37-2 4-anilinophenol 
• 1208-86-2 N-(4-methoxyphenyl)phenylamine 
• 41018-65-9 (4-methoxy-phenyl)-nitroso-phenyl-amine 

Downstream Products

• 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 
• 102316-47-2 N-benzyl-N'-(4-methoxy-phenyl)-p-phenylenediamine 
• 225381-84-0 N-(6-bromo-thieno[3,2-d]pyrimidin-4-yl)-N'-(4-methoxy-phenyl)-benzene-1,4-diamine 
• 225381-91-9 N-(4-Methoxy-phenyl)-N'-thieno[3,2-d]pyrimidin-4-yl-benzene-1,4-diamine 
• 67979-39-9 4-((4-methoxyphenyl)imino)cyclohexa-2,5-dien-1-one 
• 350-46-9 4-Fluoronitrobenzene 
• 180626-23-7 4-([D₃]methoxy)aniline 
• 4019-64-1 N,N-dimethyl-4-trideuteriomethoxy-aniline 
• 54536-23-1 1-(methoxy-d₃)-4-nitrobenzene 
• 55872-66-7 4-(benzoylamino)-4'-methoxydiphenylamine 

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.

One-pot propagation of (Hetero)Arylamines: Modular synthesis of diverse Amino-di(hetero)arylamines

Formal propagation of (hetero)arylamine is achieved via a one-pot Buchwald–Hartwig C–N cross-coupling and nitro reduction sequence, enabling a rapid modular synthesis of diverse amino-di(hetero)arylamines from (hetero)arylamines and halogenated nitrobenzenes. Various functionalized aromatic amines with different electronic and steric environments can be efficiently prolongated to formally incorporate another arylamino fragments. This approach has been successfully applied in the synthesis of more than forty amino-di(hetero)arylamines. The applicability of this method has also been demonstrated in the synthesis of oligoanilines and the tyrosine-kinase inhibitor Imatinib.

Design, synthesis and antitumor activity of novel cis-furoquinoline derivatives

A series of novel cis-furoquinoline derivatives was synthesized and tested for their antitumor activities in vitro against HepG2 cells, Lu-04 cells and Leu02 cells to evaluate structure-activity relationships. Assay-based antiproliferative activity study revealed that several compounds had significant effects on cytotoxicity, among which compounds 2f, 2l, 2q were found to be the most active compounds. Above all, compounds 2f, 2l, 2q would be potential anticancer agents which deserved further research.

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.

EPR and ENDOR spectroscopic study of the reactions of aromatic azides with gallium trichloride

The reactions of gallium trichloride with phenyl and deuterio-phenyl azides, as well as with 4-methoxyphenyl azide and deuterium isotopomers, were examined by product analysis, CW EPR spectroscopy and pulsed ENDOR spectroscopy. The products included the corresponding anilines together with 4-aminodiphenylamine type dimers, and polyanilines. Complex CW EPR spectra of the radical cations of the dimers [ArNHC6H4NH 2]+ and trimers [ArNHC6H4NHC 6H4NH2]+ were obtained. These EPR spectra were analysed with the help of data from the deuterium-substituted analogues as well as the pulse Davies ENDOR spectra. DFT computations of the radical cations provided corroborating evidence and suggested the unpaired electrons were accommodated in extensive π-delocalised orbitals. A mechanism to account for the reductive conversion of aromatic azides to the corresponding anilines and thence to the dimers and trimers is proposed.

A P,N-Ligand for palladium-catalyzed ammonia arylation: Coupling of deactivated aryl chlorides, chemoselective arylations, and room temperature reactions

(Figure Presented) Amazing ammonia: A new air-stable P,N-ligand (Mor-DalPhos) is reported that enables the palladium-catalyzed crosscoupling of ammonia to a variety of aryl chloride and aryl tosylate substrates with high chemoselectivity and, for the first time, at room temperature (see scheme; Ad = adamantyl, Ts=para-toluenesulfonyl).

Light-sensitive, diazonium group-containing polycondensation product, process for its production, and light-sensitive recording material containing this polycondensation product

A light-sensitive, diazonium group-containing polycondensation product is described which comprises (a) an optionally substituted diphenylamine-dianzonium salt I. (b) a compound corresponding to the formula II wherein R4 is H, alkyl or acyl, and R5 is an optionally substituted aromatic radical, and (c) a compound corresponding to the formula III wherein R6 and R7 are H, alkyl, or acyl and R8 is the radical of a compound selected from the group consisting of aromatic hydrocarbons, phenols, phenolethers, aromatic thioethers, aromatic heterocyclic compounds, and organic acid amides, with the radicals resulting from compound II being directing linked to the units of the diazonium salt I. In the production of the polycondensation product, I is first condensed with II and then with III. The product is suitable for use as a light-sensitive substance in recording materials, particularly in printing plates, and yields light-hardening products which have an increased oleophilicity.

Benzenesulphenanilidyl Radicals. Part 3. Reactions of 4'-Substituted Benzenesulphenanilides with t-Butoxyl Radicals

Decomposition products of the 4'-substituted benzenesulphenanilidyl radicals (2a, b, d, and e), generated from the corresponding benzenesulphenanilides (1) with t-butoxyl radicals, have been investigated in benzene, acetonitrile, and acetone.Results indicate that the decomposition modes exhibited by these radicals are not essentially influenced by variation of the solvent polarity; comparison of the findings with present and previous results from oxidation of (1) with lead dioxide show that the chemical reactivity trend displaced by the thioaminyls (2) can be greatlyinfluenced both by the reaction medium and the 4'-substituent.Evidence is presented that the benzenesulphenanilides (1b) and (1e) react in acetone in the presence of di-t-butyl hyponitrite to give products ascribable to homolytic substitution at the sulphenanilide sulphur by acetonyl radicals.