102526-87-4

Basic information

• Product Name: Benzenamine, 2,5-dimethoxy-, radical ion(1+) (9CI)
• Synonyms: Benzenamine, 2,5-dimethoxy-, radical ion(1+) (9CI)
• CAS NO: 102526-87-4
• Molecular Formula: C8H11NO2
• Molecular Weight: 153.18
• Mol File: 102526-87-4.mol
• Article Data: 31

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzenamine, 2,5-dimethoxy-, radical ion(1+) (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 2,5-dimethoxy-, radical ion(1+) (9CI)(102526-87-4)
• EPA Substance Registry System: Benzenamine, 2,5-dimethoxy-, radical ion(1+) (9CI)(102526-87-4)

Safety Data

• Hazardous Substances Data: 102526-87-4(Hazardous Substances Data)

Upstream product

• 89-39-4 1,4-dimethoxy-2-nitrobenzene 
• 103860-38-4 2,5-dimethoxyphenylurea 
• 150-78-7 1,4-dimethoxybezene 
• 23997-82-2 2,5-dimethoxyphenyl methyl ketone oxime 
• 56309-62-7 2,5-dimethoxyphenyl isocyanate 
• 2150-46-1 Methyl 2,5-dihydroxybenzoate 
• 2785-98-0 2,5-dimethoxybenzoic acid 
• 2150-40-5 methyl 2,5-dimethoxybenzoate 
• 67184-41-2 2,5‐dimethoxybenzaldoxime 
• 1208328-54-4 N-hydroxy-2,5-dimethoxy-benzamide 
• 3467-59-2 2,5-dimethoxyacetanilide 
• 67-56-1 methanol 
• 91-23-6 2-Nitroanisole 
• 15791-03-4 1,1,4,4-tetramethoxycyclohexa-2,5-diene 

Downstream Products

• 3224-54-2 2-Methoxyphenazin-5-oxid 
• 13860-45-2 1,4-Dimethoxy-phenazin 
• 36098-07-4 2,5-Dimethoxy-2',4'-dinitrodiphenylamin 
• 4031-94-1 2,5-dimethoxy-N,N-dimethylaniline 
• 708240-48-6 N,N'-bis-(2,5-dimethoxy-phenyl)-thiourea 
• 94459-25-3 N-(2,5-dimethoxy-phenyl)-glycine nitrile 
• 99986-85-3 lactic acid-(2,5-dimethoxy-anilide) 
• 40532-06-7 2-isothiocyanato-1,4-dimethoxybenzene 
• 4914-21-0 (2,5-dimethoxy-phenyl)-carbamic acid-(4-chloro-but-2-ynyl ester) 
• 92852-60-3 4-(4-amino-2,5-dimethoxy-phenylazo)-benzaldehyde 
• 101585-17-5 p-tolyloxy-acetic acid-(2,5-dimethoxy-anilide) 

Relevant articles and documents

Methoxy and bromo scans on N-(5-methoxyphenyl) methoxybenzenesulphonamides reveal potent cytotoxic compounds, especially against the human breast adenocarcinoma MCF7 cell line

Thirty seven N-(5-methoxyphenyl)-4-methoxybenzenesulphonamide with methoxy or/and bromo substitutions (series 1-4) and with different substituents on the sulphonamide nitrogen have been synthesised. 21 showed sub-micromolar cytotoxicity against HeLa and HT-29 human tumour cell lines, and were particularly effective against MCF7. The most potent series has 2,5-dimethoxyanilines, especially the 4-brominated compounds 23–25. The active compounds inhibit microtubular protein polymerisation at micromolar concentrations, thus pointing at tubulin as the target. Co-treatment with the MDR inhibitor verapamil suggests that they are not MDR substrates. Compound 25 showed nanomolar antiproliferative potency. It severely disrupts the microtubule network in cells and arrests cells at the G2/M cell-cycle phase, thus confirming tubulin targeting. 25 triggered apoptotic cell death, and induced autophagy. Docking studies suggest binding in a distinct way to the colchicine site. These compounds are promising new antitumor agents acting on tubulin.

Nitroethane in polyphosphoric acid: A new reagent for acetamidation and amination of aromatic compounds

A new method of acetamidation of aromatic compounds based on their reaction with nitroethane in polyphosphoric acid has been developed. Upon the hydrolysis of acetamides during the reaction mixture workup, the corresponding amines can be obtained. Georg Thieme Verlag Stuttgart New York.

Phenylureas. Part 2. Mechanism of the acid hydrolysis of phenylureas

The mechanism of the hydrolytic decomposition of phenylureas in acid media is investigated. It includes, in part, knowledge already present in the literature. Over the investigated pH range the occurrence of a rate maximum in the pH curves due to the strongly reduced water activity at higher acid strengths is observed. An addition-elimination mechanism with rate-determining attack of water at the N-protonated substrate is proposed. The reversion of the substituent influence on the reaction rate with increasing acidity of the reaction medium points to a change of the hydrolytic decomposition mechanism in strongly acidic media.

Convenient synthesis of 3-amino-2-hydroxy-5-methylbenzenesulfonic acid

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AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS

In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds

Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C-C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (-NH2) and hydroxyl (-OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N-H and N-alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.