59557-91-4

Basic information

• Product Name: 4-BROMO-2-METHOXY-PHENYLAMINE
• Synonyms: 4-BROMO-2-METHOXY-PHENYLAMINE;4-BROMO-2-METHOXYANILINE;4-BROMO-2-METHOXYANILINE[2-AMINO-5-BROMOANISOLE] ;2-Amino-5-bromoanisole;4-bromo-o-anisidine;4-Bromo-2-methoxyaniline 99%;2-Amino-5-bromoanisole, 4-Bromo-o-anisidine;4-Bromo-o-anisidine 2-Amino-5-bromoanisole
• CAS NO: 59557-91-4
• Molecular Formula: C₇H₈BrNO
• Molecular Weight: 202.05
• EINECS: 200-002-4
• Product Categories: Aniline;C2 to C8;Amines;Building Blocks;C7;Chemical Synthesis;Ethers;New Products for Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Oxygen Compounds
• Mol File: 59557-91-4.mol
• Article Data: 41

Chemical Properties

• Melting Point: 59 °C
• Boiling Point: 250.4 °C at 760 mmHg
• Flash Point: 105.2 °C
• Appearance: /
• Density: 1.531 g/cm³
• Vapor Pressure: 0.0218mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Soluble in methanol.
• PKA: 3.83±0.10(Predicted)
• CAS DataBase Reference: 4-BROMO-2-METHOXY-PHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-2-METHOXY-PHENYLAMINE(59557-91-4)
• EPA Substance Registry System: 4-BROMO-2-METHOXY-PHENYLAMINE(59557-91-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43-52
• Safety Statements: 36/37
• RIDADR: UN2811/6.1/IIIPG
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 59557-91-4(Hazardous Substances Data)

Usage

Chemical Properties

Black particles

Uses

4-Bromo-2-methoxyaniline is used as a reagent in the synthesis of 3,5-diamino-1,2,4-triazole ureas as potent anaplastic lymphoma kinase (ALK) inhibitors. It is also used as a reagent in the synthesis of chroman-3-amides as potent Rho kinase inhibitors. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff fields.

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

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

Downstream Products

• 791642-68-7 4-bromo-1-iodo-2-methoxybenzene 
• 103028-32-6 6-bromo-8-methoxy-quinoline 
• 99465-23-3 (E)-N-(4-Bromo-2-methoxy-phenyl)-3-ethoxy-acrylamide 
• 262433-01-2 (4-bromo-2-methoxyphenyl)carbamic acid tert-butyl ester 
• 495406-62-7 methyl 2-[(4-bromo-2-methoxyphenyl)amino]but-2-enedioate 
• 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 
• 1264728-46-2 4-bromo-2-methoxy-1-(bisacetoxyiodo)benzene 
• 889849-21-2 (4-bromo-2-methoxyphenyl)boronic acid 
• 1264728-53-1 4-(4-bromo-2-methoxyphenoxy)-3,6-di((S)-sec-butyl)-3-hydroxy-1-methoxypiperazine-2,5-dione 
• 1264728-54-2 4-(4-bromo-2-methoxyphenoxy)-3,6-di((S)-sec-butyl)-1,3-dimethoxypiperazine-2,5-dione 
• 90965-63-2 4-bromocyclohexa-3,5-diene-1,2-dione 

Relevant articles and documents

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.

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.

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.