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

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

Downstream Products

• 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 
• 227305-15-9 4-Bromo-2-methoxyphenyldiazonium tetrafluoroborate 
• 227305-07-9 4-bromo-2-methoxy-1,1'-biphenyl 
• 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 
• 1275599-59-1 N-(2-hydroxy-4-(2-morpholino-4-oxo-4H-chromen-8-yl)phenyl)-2-morpholinoacetamide 
• 461699-81-0 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 
• 1379464-80-8 N-(4-bromo-2-methoxyphenyl)-2-((4-nitrophenyl)thio)benzamide 
• 1608997-47-2 (E)-5-ammonio-3-(2-(4-bromo-2-methoxyphenyl)hydrazono)-4-oxo-3,4-dihydronaphthalene-2,7-disulfonate 

Relevant articles and documents

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.