27151-54-8

Usage

Uses

Used in Chemical Synthesis:
4-(4-Methoxyanilino)phenol is used as a chemical intermediate for the production of 4,4''-Iminodiphenol (I409010), which is derived from 4,4''-Dimethoxydiphenylamine (D461065). This diphenylamine derivative is utilized as a chemical additive in the curing process of rubber, enhancing the product's properties and performance.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(4-Methoxyanilino)phenol is used as a building block for the synthesis of various drugs. Its unique chemical structure allows it to be a versatile component in the development of new medications, potentially contributing to the treatment of various health conditions.
Used in Dye Manufacturing:
4-(4-Methoxyanilino)phenol is also employed in the manufacturing of dyes due to its reactive nature. It can be used to produce a range of colors, which can be applied in various industries such as textiles, plastics, and printing.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 1762, 1955 DOI: 10.1021/ja01612a012

InChI:InChI=1/C13H13NO2/c1-16-13-8-4-11(5-9-13)14-10-2-6-12(15)7-3-10/h2-9,14-15H,1H3

Upstream product

• 104-94-9 4-methoxy-aniline 
• 123-31-9 hydroquinone 
• 696-62-8 para-iodoanisole 
• 123-30-8 4-amino-phenol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 100-17-4 para-methoxynitrobenzene 
• 108-95-2 phenol 

Downstream Products

• 632384-54-4 potassium [4-(4-methoxyphenylamino)phenoxy]acetate 
• 632380-83-7 C₁₆H₁₆N₂O₅ 

Relevant academic research and scientific papers

"on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols

The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.

The invention relates to a N, N - disubstituted hydrazide as ligand copper catalysis C - N coupling method (by machine translation)

The invention discloses a to N, N - disubstituted hydrazide as ligand copper catalysis C - N coupling method, the method uses the aromatic halides with amine compound as a raw material, in order to alcohol compound as the solvent, in order to copper or copper compound as a catalyst, in order to as formula I or formula II as shown by a N, N - disubstituted hydrazide as a ligand, the presence of a base, in the 10 - 130 °C generating C - N coupled reaction for generating N - aryl compound: the invention mild reaction conditions, high chemical selectivity, substrate and wide range of application, simplicity of operation, product is simple and easy to separation and environmental protection, the obtained product yield is higher. Wherein R1, R2 is selected from methyl, phenyl, 4 - methoxyphenyl, 4 - nitro-phenyl, 2 - methylphenyl, 2 - isopropyl phenyl; R3 is hydrogen or methoxy. (by machine translation)

Room-Temperature CuI-Catalyzed Amination of Aryl Iodides and Aryl Bromides

A general and effective CuI/N′,N′-diaryl-1H-pyrrole-2-carbohydrazide catalyst system was developed for the amination of aryl iodides and bromides at room temperature with good chemoselectivity between -OH and -NH2 groups. Only 5 mol % of CuI and ligands was needed in this protocol to effect the amination of various aryl bromides and aryl iodides with a wide range of aliphatic and aryl amines (1.3 equiv).