59557-91-4

Usage

Uses

Used in Pharmaceutical Industry:
4-BROMO-2-METHOXY-PHENYLAMINE is used as a reagent for the synthesis of 3,5-diamino-1,2,4-triazole ureas, which are potent anaplastic lymphoma kinase (ALK) inhibitors. These inhibitors are essential in the treatment of various cancers, as they help regulate the abnormal cell growth associated with these diseases.
4-BROMO-2-METHOXY-PHENYLAMINE is also used as a reagent in the synthesis of chroman-3-amides, which are potent Rho kinase inhibitors. Rho kinase inhibitors have potential applications in the treatment of various conditions, including cardiovascular diseases, neurological disorders, and cancer.
Used in Agrochemical Industry:
As an important raw material and intermediate, 4-BROMO-2-METHOXY-PHENYLAMINE is utilized in the development of agrochemicals, which are essential for enhancing crop productivity and protecting plants from pests and diseases.
Used in Dyestuff Industry:
4-BROMO-2-METHOXY-PHENYLAMINE is employed in the production of various dyes, which are used in different applications such as textiles, plastics, and printing inks. Its unique chemical properties contribute to the development of dyes with specific color characteristics and performance attributes.
Used in Organic Synthesis:
4-BROMO-2-METHOXY-PHENYLAMINE is a vital intermediate in organic synthesis, where it is used to create a wide range of compounds with diverse applications in various industries. Its versatility and reactivity make it a valuable component in the synthesis of complex organic molecules.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 32, p. 1936, 1989 DOI: 10.1021/jm00128a041

InChI:InChI=1/C7H8BrNO/c1-10-7-4-5(8)2-3-6(7)9/h2-4H,9H2,1H3

Upstream product

• 106951-33-1 N,N'-bis-(4-bromo-2-methoxy-phenyl)-urea 
• 5329-15-7 N-(4-amino-2-methoxyphenyl)acetamide 
• 90-04-0 2-methoxy-phenylamine 
• 93-27-6 5-nitro-2-acetylaminoanisole 
• 20244-61-5 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one 
• 226713-37-7 4-bromo-2-methoxyaniline hydrobromide 
• 103966-66-1 4-bromo-2-methoxy-1-nitro-benzene 
• 103291-07-2 4-bromo-1-fluoro-2-methoxy-benzene 
• 67-56-1 methanol 
• 586-78-7 para-nitrophenyl bromide 
• 321-23-3 4-bromo-2-fluoronitrobenzene 
• 1226-63-7 1,3-bis(2-methoxyphenyl)urea 

Downstream Products

• 143360-01-4 N-(4-bromo-2-methoxyphenyl)acetamide 
• 99465-23-3 (E)-N-(4-Bromo-2-methoxy-phenyl)-3-ethoxy-acrylamide 
• 89446-10-6 ethyl 3-<(4-bromo-2-methoxyphenyl)imino>butyrate 
• 16817-43-9 5-Bromo-2-chloroanisole 
• 495406-62-7 methyl 2-[(4-bromo-2-methoxyphenyl)amino]but-2-enedioate 
• 227305-15-9 4-Bromo-2-methoxyphenyldiazonium tetrafluoroborate 
• 227305-07-9 4-bromo-2-methoxy-1,1'-biphenyl 
• 1027709-71-2 N-[4-bromo-2-(methyloxy)phenyl]-1,3-thiazole-4-carboxamide 
• 1130037-46-5 [cyano-14C]4-cyano-2-methoxyphenylamine 
• 1041261-15-7 2-methoxy-4-(6-methoxy-2-naphthyl)aniline 
• 177476-76-5 4-amino-3-methoxybenzonitrile 
• 708249-64-3 C₁₃H₁₂BrNO₃S 
• 1246533-01-6 N₂-(4-bromo-2-methoxy-phenyl)-N₆-cyclohexyl-9H-purine-2,6-diamine 
• 1275599-59-1 N-(2-hydroxy-4-(2-morpholino-4-oxo-4H-chromen-8-yl)phenyl)-2-morpholinoacetamide 

Relevant academic research and scientific papers

Methoxy aniline compound and synthesis method thereof

The invention mainly relates to a preparation method of anisidine. According to the technical scheme, under the promotion of the photocatalyst and blue light, in the argon atmosphere, nitro compounds and methanol generate methoxyaniline, wherein products and additional products with stable molecular structures and excellent chemical properties are prepared, wherein a photocatalyst and a blue light source are used in the method, and a new path is provided for synthesis of methoxyaniline compounds. The method has the characteristics of mild reaction conditions, simple reaction system, less reaction equipment, simplicity and convenience in experimental operation and the like. The methoxyaniline derivative and the synthetic method thereof can be applied to a plurality of industrial production fields of dyes, pesticides, medicines, rubber additives and the like. The method is particularly suitable for scientific research, development and utilization of efficient and selective synthesis of methoxyaniline compounds by a one-pot method.

Preparation method of 2-amino-3-methoxy-5-bromobenzonitrile

The invention discloses a preparation method of 2-amino-3-methoxy-5-bromobenzonitrile. The method comprises the following steps: (1) reacting a compound (II) with sodium methoxide to generate a compound (III); (2) carrying out reduction treatment on the compound (III) to obtain a compound (IV); (3) reacting the compound (IV) with trichloroacetaldehyde hydrate and hydroxylamine hydrochloride to generate a compound (V); (4) reacting the compound (V) with concentrated sulfuric acid to generate a compound (VI); (5) preparing a compound (VII) from the compound (VI) under the conditions of hydrogenperoxide and sodium hydroxide; (6) reacting the compound (VII) with acyl chloride to generate a compound (VIII); (7) reacting the compound (VIII) with ammonia water to generate a compound (IX); and (8) reacting the compound (IX) in the presence of phosphorus pentoxide to generate 2-amino-3-methoxy-5-bromobenzonitrile. The preparation method provided by the invention is higher in yield.

Nucleophilic aromatic substitution of unactivated fluoroarenes enabled by organic photoredox catalysis

Nucleophilic aromatic substitution (SNAr) is a classical reaction with well-known reactivity toward electron-poor fluoroarenes. However, electron-neutral and electron-rich fluoro(hetero)arenes are considerably underrepresented. Herein, we present a method for the nucleophilic defluorination of unactivated fluoroarenes enabled by cation radical-accelerated nucleophilic aromatic substitution. The use of organic photoredox catalysis renders this method operationally simple under mild conditions and is amenable to various nucleophile classes, including azoles, amines, and carboxylic acids. Select fluorinated heterocycles can be functionalized using this method. In addition, the late-stage functionalization of pharmaceuticals is also presented. Computational studies demonstrate that the site selectivity of the reaction is dictated by arene electronics.

Sodium sulfate-hydrogen peroxide-sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones

The regioselective bromination and iodination of unprotected aromatic primary amines using enclathrated hydrogen peroxide as an oxidant under mild conditions has been developed, in which potassium bromide (KBr) and potassium iodide (KI) were used as brominating and iodinating agents, respectively. The adduct shows not only regioselectivity for para- or ortho-isomers but also a remarkable chemoselectivity for monobromination. Selective oxidation of sulfides to sulfoxides and sulfones has also been studied and good to excellent yields of the desired products were obtained. Acetic acid was found to be the solvent of choice for these reactions. This simple method represents an ecologically benign and alternative pathway for the oxidative halogenation of anilines and the oxidation of sulfides to sulfoxides and sulfones.

Cu-mediated selective bromination of aniline derivatives and preliminary mechanism study

A simple and efficient bromination of aniline, aniline derivatives, and analogs have been developed. Forty three examples were given and the highest yield reached was 98%. Different substrates including substituted aniline, pyridin-amine, N-substituted aniline, N,N-disubstituted aniline, N-phenyl-amide, N-phenyl-sulfonamide, and nitrogen-containing heterocycles were all reactive and selectively generated desired bromo-products. The method can be applied to synthesize drug intermediate and quinoxaline derivatives.

EGFR tyrosine kinase of selective inhibitors of clinically significant mutant

Kinase can be prevented by the compound and the salt, especially epidermal growth factor receptor (EGFR,erbB-2,erbB-4) and kinase clinica important gatekeeper 'mutant'; and abnormal cell profilerative diseases such as cancers can be treated or improved.

Development of the “hidden” multifunctional agents for Alzheimer's disease

Alzheimer's disease (AD)is a chronic, fatal and complex neurodegenerative disorder, which is characterized by cholinergic system dysregulation, metal dyshomeostasis, amyloid-β (Aβ)aggregation, etc. Therefore in most cases, single-target or single-function

AHR INHIBITORS AND USES THEREOF

The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.

o-xylylene bis(triethyl ammonium tribromide) as a mild and recyclable reagent for rapid and regioselective bromination of anilines and phenols

Background: o-Xylylene bis(triethyl ammonium tribromide) (OXBTEATB) as a recyclable and high bromine containing di-(tribromide) reagent has been employed for the bromination of various organic substrates such as phenol and aniline or its derivatives. This catalyst can be recovered and reused several times. Methods: Aryl bromides shown in Table 1, were easily produced from bromination of aromatic compounds by OXBTEATB. This high-yield process lets the reagents to be recycled and reused. Results: As shown in Table 1, substituted anilines, phenols and β-naphthol were found to be the most reactive and immediately converted to the corresponding mono-brominated products by OXBTEATB. Conclusion: OXBTEATB can be considered a solidified bromine. This novel reagent has variable solubility in different polar protic and aprotic solvents but insoluble in non-polar aprotic solvent. Subsequently, OXBTEATB can be recognized as a more useful brominating and regioselective catalyst than the liquid bromine.

2,4-DISUBSTITUTED PHENYLENE-1,5-DIAMINE DERIVATIVES AND APPLICATIONS THEREOF, AND PHARMACEUTICAL COMPOSITIONS AND PHARMACEUTICALLY ACCEPTABLE COMPOSITIONS PREPARED THEREFROM

The present invention provides a class of 2,4-substituted phenylene-1,5-diamine derivatives, having an inhibiting effect on EGFR tyrosine kinases, and pharmaceutically acceptable salt, stereoisomer, solvate or prodrug of said derivatives. See the description for the definition of each group in the formula. In addition, the present invention also discloses pharmaceutical compositions, pharmaceutically acceptable compositions and applications thereof.